4-Hydroxybutanoic acid (GHB) by Asch

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PubChem

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Reactions (65)

Yield

Substances (18)

Citations (74)

Conditions

References

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Rx-ID: 47490 Find similar reactions

With hydrogenchloride; sodium amalgam; diethyl ether

die Saeure bezw.ihr Lacton, das Butyrolacton entsteht;

Fichter; Herbrand

Chemische Berichte, 1896 , vol. 29, p. 1193 Full Text View citing articles Show Details

With hydrogen; nickel

die Saeure bezw.ihr Lacton, das Butyrolacton entsteht;

Eijkman

Chem. Zentralbl., 1907 , vol. 78, # I p. 1617 Full Text Show Details

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die Saeure bezw.ihr Lacton, das Butyrolacton entsteht;

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Rx-ID: 165371 Find similar reactions

Bentley; Haworth; Perkin

Journal of the Chemical Society, 1896 , vol. 69, p. 175 Full Text View citing articles Show Details

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Rx-ID: 178540 Find similar reactions

Henry

Bulletin de la Societe Chimique de France, 1886 , vol. <2>45, p. 341 Chem. Zentralbl., 1898 , vol. 69, # II p. 273 Full Text Show Details

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Rx-ID: 223325 Find similar reactions

With water; silver(l) oxide

Paul

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1942 , vol. 215, p. 304 Full Text Show Details

Paul; Tchelitcheff

Bulletin de la Societe Chimique de France, 1948 , p. 197,202 Full Text Show Details

With air

T=60°C; isoliert als γ-Butyrolacton;

Adkins; Krsek

Journal of the American Chemical Society, 1948 , vol. 70, p. 385 Journal of the American Chemical Society, 1949 , vol. 71, p. 3053,3054 Full Text Show Details

With nicotinamide adenine dinucleotide; aldehyde dehydrogenase

Enzymatic reaction;

Lenz, Daniel; Juebner, Martin; Bender, Katja; Wintermeyer, Annette; Beike, Justus; Rothschild, Markus A.; Kaeferstein, Herbert

Naunyn-Schmiedeberg's Archives of Pharmacology, 2011 , vol. 383, # 6 p. 647 - 654 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 227294 Find similar reactions

With sodium ethanolate

das Lacton entsteht;

Marvel; Birkhimer

Journal of the American Chemical Society, 1929 , vol. 51, p. 261 Full Text View citing articles Show Details

With thionyl chloride in benzyl alcohol

Avantgarde S.p.A.

Patent: US5627212 A1, 1997 ;

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Title/Abstract Full Text Show Details

2.a:Preparation of the ester of acetyl L-carnitine with γ-hydroxybutyric acid (ST 793)

Step a: Preparation of the benzyl ester of γ-bromobutyric acid (ST 793). γ-bromobutyric acid (3.3 g; 0.02 moles) was suspended in benzyl alcohol (15 mL). The suspension was cooled to 0° C. and thionyl chloride (8 mL; 0.01 moles) was slowly added dropwise thereto. The resulting mixture was kept at room temperature for 16 hours, then concentrated under vacuum to remove the unreacted thionyl chloride and distilled to remove the benzyl alcohol. The distillation residue was purified by silica gel chromatography using hexane-AcOEt 98:2 as eluant. TLC hexane RF =0-2 NMR CDCl3 δ 7.2(5H,s,aromatic); 5.0(2H,s,CH2 -benzyl) 3.3(2H,t,CH2 COO); 2.6-2.0(4H,m,BrCH2 CH2)

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die Saeure bezw.ihr Lacton, das Butyrolacton entsteht;

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Rx-ID: 234871 Find similar reactions

Willstaetter

Chemische Berichte, 1902 , vol. 35, p. 602 Full Text Show Details

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das Natriumsalz reagiert.Electrolysis;

die Saeure bezw.ihr Lacton, das Butyrolacton entsteht;

Hamonet

Bulletin de la Societe Chimique de France, 1905 , vol. <3>33, p. 530 Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1904 , vol. 138, p. 1611 Full Text Show Details

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Rx-ID: 269739 Find similar reactions

Fittig; Roeder

Justus Liebigs Annalen der Chemie, 1885 , vol. 227, p. 19 Full Text Show Details

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die Saeure bezw.ihr Lacton, das Butyrolacton entsteht;

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Rx-ID: 531300 Find similar reactions

Willstaetter

Chemische Berichte, 1902 , vol. 35, p. 602 Full Text Show Details

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With sodium amalgam; diethyl ether; acetic acid

die Saeure bezw.ihr Lacton, das Butyrolacton entsteht;

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Rx-ID: 659461 Find similar reactions

Saizew,A.

Justus Liebigs Annalen der Chemie, 1874 , vol. 171, p. 261 Journal fuer Praktische Chemie (Leipzig), 1882 , vol. <2>25, p. 64 Full Text Show Details

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Rx-ID: 845896 Find similar reactions

With ethanol

Verseifen des gebildeten Nitrils mit Kalilauge; die Saeure bezw.ihr Lacton, das Butyrolacton entsteht;

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Fruehling

Monatshefte fuer Chemie, 1882 , vol. 3, p. 697 Full Text Show Details

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35%

With sodium hydroxide

With sodium hydroxide in dimethyl sulfoxide

0.416667 h; ΔH; other solvent; Thermodynamic data;

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Rx-ID: 882152 Find similar reactions

Wiberg, Kenneth B.; Waldron, Roy F.

Journal of the American Chemical Society, 1991 , vol. 113, # 20 p. 7697 - 7705 Title/Abstract Full Text View citing articles Show Details

Wiberg, Kenneth B.; Waldron, Roy F.

Journal of the American Chemical Society, 1991 , vol. 113, # 20 p. 7697 - 7705 Title/Abstract Full Text View citing articles Show Details

(i) aq. NaOH, EtOH, (ii) HCl, MeOH; Multistep reaction;

Dafforn,G.A.; Koshland,D.E.

Journal of the American Chemical Society, 1977 , vol. 99, p. 7246 - 7257 Full Text View citing articles Show Details

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With potassium hydroxide in methanol

Heating;

Tori, Motoo; Toyoda, Naoko; Sono, Masakazu

Journal of Organic Chemistry, 1998 , vol. 63, # 2 p. 306 - 313 Title/Abstract Full Text View citing articles Show Details

With hydrogenchloride

T=35°C; KineticsEquilibrium constant; Further Variations:TemperaturespH-values;

Perez-Prior, M. Teresa; Manso, Jose A.; Del Pilar Garcia-Santos; Calle, Emilio; Casado, Julio

Journal of Organic Chemistry, 2005 , vol. 70, # 2 p. 420 - 426 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide in water

Naeser, Ulrike; Pierik, Antonio J.; Scott, Richard; Cinkaya, Irfan; Buckel, Wolfgang; Golding, Bernard T.

Bioorganic Chemistry, 2005 , vol. 33, # 1 p. 53 - 66 Title/Abstract Full Text View citing articles Show Details

With recombinant L-pantolactone hydrolase (A.tumefaciens Lu681); 2,2'-piperazine-1,4-diyl-bis-ethanesulfonic acid

T=30°C; pH=7.0; Enzymatic reaction;

Kesseler, Maria; Friedrich, Thomas; Hoeffken, Hans Wolfgang; Hauer, Bernhard

Advanced Synthesis and Catalysis, 2002 , vol. 344, # 10 p. 1103 - 1110 Title/Abstract Full Text View citing articles Show Details

With serum lactonase

Enzymatic reaction;

Lenz, Daniel; Juebner, Martin; Bender, Katja; Wintermeyer, Annette; Beike, Justus; Rothschild, Markus A.; Kaeferstein, Herbert

Naunyn-Schmiedeberg's Archives of Pharmacology, 2011 , vol. 383, # 6 p. 647 - 654 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide in water

T=70°C; 16 h;

Lin, You-Han; Lai, Chien-Chen; Liu, Yi-Hung; Peng, Shie-Ming; Chiu, Sheng-Hsien

Angewandte Chemie - International Edition, 2013 , vol. 52, # 39 p. 10231 - 10236 Angew. Chem., 2013 , vol. 125, # 39 p. 10421 - 10426,6 Title/Abstract Full Text View citing articles Show Details

With water; sodium hydroxide

Zhai, Duanting; Tan, Yong Qiao Elton; Xu, Wang; Chang, Young-Tae

Chemical Communications, 2014 , vol. 50, # 22 p. 2904 - 2906 Title/Abstract Full Text View citing articles Show Details

With Acinetobacter sp SE19 lactonase; 5'ATP; NADH; magnesium chloride; zinc(II) chloride in aq. phosphate buffer

T=20°C; pH=6.8; Enzymatic reaction; Hide Experimental Procedure

INVISTA North America S.á.r.l.; Botes, Adriana Leonora; Conradie, Alex Van Eck

Patent: US2016/222420 A1, 2016 ; Location in patent: Paragraph 0166 ; Title/Abstract Full Text Show Details

Enzyme activity assays (i.e., from y-butyrolactone via 4-hydroxybutyrate to 4-hydroxybutanal) were performed in duplicate in a buffer composed of a final concentration of 50mM potassium phosphate buffer (pH=6.8), 75 tM ZnC12,1.25 mgmL Acinetobacter sp SE1 9 lactonase, 10 mM y-butyrolactone, 10mM MgC12, 1 mMATP and 0.5mM NADPH. Each enzyme activity assay reaction was initiated by adding purified carboxylate reductase and phosphopantetheine transferase gene products or the empty vector control to the assay buffer containing the 4-hydroxybutyrate formed from y-butyrolactone and then incubated at room temperature for 1 hout The consumption of NADPH was monitored by absorbance at 340 nm. Each enzyme only control without y-butyrolactone demonstrated low base line consumption of NADPH. See bars for A13K756S4.1, EFV11917.1 and ADG9S14O.1 in FIG. 6.

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90%

With sodium tetrahydroborate in water

12 h; Ambient temperature;

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Rx-ID: 1890353 Find similar reactions

Bianco, A.; Passacantilli, P.; Righi, G.

Synthetic Communications, 1988 , vol. 18, # 15 p. 1765 - 1772

Title/Abstract Full Text Show Details

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With K2[PtCl6]; dipotassium tetrachloroplatinate; oxygen in water-d2

T=80 - 90°C; 144 h; other aliphatic carboxylic acids; also without Pt(IV)-catalyst; Mechanism;

Kao, Lien-Chung; Sen, Ayusman

Journal of the Chemical Society, Chemical Communications, 1991 , # 18 p. 1242 - 1243 Title/Abstract Full Text View citing articles Show Details

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A: 70 % Spectr. B: 30 % Spectr.

With hydrogenchloride; sodium nitrite in water

24 h; Ambient temperature;

Gouesnard, Jean-Paul

Bulletin de la Societe Chimique de France, 1989 , # 1 p. 88 - 94 Title/Abstract Full Text Show Details

A: 70 % Spectr. B: 30 % Spectr.

With hydrogenchloride; sodium nitrite in water

24 h; Ambient temperature;

Gouesnard, Jean-Paul

Bulletin de la Societe Chimique de France, 1989 , # 1 p. 88 - 94 Title/Abstract Full Text Show Details

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Rx-ID: 5461710 Find similar reactions

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Fittig; Chanlarow

Justus Liebigs Annalen der Chemie, 1884 , vol. 226, p. 331,332 Full Text View citing articles Show Details

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T=25°C; und 39grad und 50grad.Hydrolysis; Rate constant;

Rx-ID: 5461711 Find similar reactions

Coffin; Long

Journal of the American Chemical Society, 1952 , vol. 74, p. 5767 Full Text View citing articles Show Details

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Hide Experimental Procedure

Rx-ID: 6934966 Find similar reactions

Kuhnle et al.

Journal of the Chemical Society, Chemical Communications, 1972 , p. 287 Full Text View citing articles Show Details

Baschkirow et al.

Neftekhimiya, 1970 , vol. 10, p. 569 Chem.Abstr., 1970 , vol. 73, # 109227 Full Text Show Details

Sankyo Company, Limited

Patent: US5624935 A1, 1997 ; Title/Abstract Full Text Show Details

32:4-Hydroxybutyric acid

PREPARATION 32 4-Hydroxybutyric acid A 2N aqueous solution of sodium hydroxide was added to a solution of 10.0 g of γ-butyrolactone in 100 ml of methanol, and the resulting mixture was allowed to stand overnight. At the end of this time, the reaction mixture was neutralized by adding 2N aqueous hydrochloric acid, after which it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, to give 3.70 g of the title compound as an oil.

Pfizer Inc.

Patent: US4814342 A1, 1989 ;

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Title/Abstract Full Text Show Details

29:hydroxybutyrate

hydroxybutyrate A solution of 459 mg of the Rf 0.32 product of Example 29B in 2 ml ether at 0° C. was treated with 1.92 mL methylmagnesium bromide (1.9M in n-butyl ether). After 10 minutes at 0° C. 1 mL saturated aqueous ammonium chloride was added. The mixture was extracted with ether which was washed with 1N HCl, aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, concentrated and the residue chromatographed on silica (ether-hexanes) giving 375 mg of a colorless solid. Hide Details

AVANTGARDE S.p.A.

Patent: EP631779 A1, 1995 ;

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Title/Abstract Full Text Show Details

Particularly preferred are the esters of the following hydroxyacids: ... α - hydroxyisobutyric acid β - hydroxybutyric acid γ - hydroxybutyric acid α - hydroxyisocaproic acid ...

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Rx-ID: 6934967 Find similar reactions

With barium dihydroxide

die Saeure bezw.ihr Lacton, das Butyrolacton entsteht;

Fittig; Chanlarow

Justus Liebigs Annalen der Chemie, 1884 , vol. 226, p. 331,332 Full Text View citing articles Show Details

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Rx-ID: 6934968 Find similar reactions

durch Verseifung; die Saeure bezw.ihr Lacton, das Butyrolacton entsteht;

Michael

Chemische Berichte, 1901 , vol. 34, p. 4044 Full Text Show Details

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Rx-ID: 6934969 Find similar reactions

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Bentley; Haworth; Perkin

Journal of the Chemical Society, 1896 , vol. 69, p. 175 Full Text View citing articles Show Details

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Rx-ID: 6934970 Find similar reactions

Adkins; Krsek

Journal of the American Chemical Society, 1948 , vol. 70, p. 385 Journal of the American Chemical Society, 1949 , vol. 71, p. 3053,3054 Full Text Show Details

T=60°C;

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Rx-ID: 6934971 Find similar reactions

With sodium amalgam

die Saeure bezw.ihr Lacton, das Butyrolacton entsteht;

Perkin; Sprankling

Journal of the Chemical Society, 1899 , vol. 75, p. 17 Full Text View citing articles Show Details

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Rx-ID: 6934972 Find similar reactions

die Saeure bezw.ihr Lacton, das Butyrolacton entsteht;

Fittig; Roeder

Justus Liebigs Annalen der Chemie, 1885 , vol. 227, p. 19 Full Text Show Details

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Rx-ID: 6934973 Find similar reactions

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Paul

Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1942 , vol. 215, p. 304 Full Text Show Details

Paul; Tchelitcheff

Bulletin de la Societe Chimique de France, 1948 , p. 197,202 Full Text Show Details

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Synthesize Find similar Rx-ID: 7058294 Find similar reactions

Chanlarow

Justus Liebigs Annalen der Chemie, 1884 , vol. 226, p. 326 Full Text Show Details

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A: 22% B: 24 % Spectr.

With carbon monoxide; oxygen; trifluoroacetic acid; palladium on activated charcoal; copper dichloride

T=75°C; Hydroxylation; P=56887.8 Torr; 18 h; Title compound not separated from byproducts.;

Shen, Chengyu; Garcia-Zayas, Eduardo A.; Sen, Ayusman

Journal of the American Chemical Society, 2000 , vol. 122, # 17 p. 4029 - 4031 Title/Abstract Full Text View citing articles Show Details

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63%

With hydrogenchloride in water

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Rx-ID: 10127123 Find similar reactions

Iliev, Boyan; Linden, Anthony; Heimgartner, Heinz

Helvetica Chimica Acta, 2006 , vol. 89, # 1 p. 153 - 175 Title/Abstract Full Text View citing articles Show Details

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With rat brain voltage-dependent potassium channel Kvβ2subunit-bound NADPH in ethanol

T=22°C; pH=7.5; aq. phosphate bufferEnzymatic reaction; Kinetics;

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Rx-ID: 32078667 Find similar reactions

Alka, Kumari; Ryan, Barry J.; Dolly, J. Oliver; Henehan, Gary T.M.

International Journal of Biochemistry and Cell Biology, 2010 , vol. 42, # 12 p. 2012 - 2018 Title/Abstract Full Text View citing articles Show Details

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30 %Chromat.

With Co(II)DPDME; oxygen; isovaleraldehyde in acetonitrile

T=60°C; 0.5 h;

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Rx-ID: 33461714 Find similar reactions

Sun, Chengguo; Hu, Bingcheng; Liu, Zuliang

Heteroatom Chemistry, 2012 , vol. 23, # 3 p. 295 - 303 Title/Abstract Full Text View citing articles Show Details

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With 1 Pd/Sibunit; oxygen in water

T=100°C; P=2250.23 Torr; 24 h; Hide Experimental Procedure

Ryabenkova, Yulia; Miedziak, Peter J.; Knight, David W.; Taylor, Stuart H.; Hutchings, Graham J.

Tetrahedron, 2014 , # 36 p. 6055 - 6058 Title/Abstract Full Text Show Details

Butanediol oxidation

General procedure: Reactions were carried out using a Radley’s low pressure glass reactor (50 ml). A butanediol in water (20 ml, 0.6 M) and the catalyst(butanediol/metal ratio2000) were added into the reactor,which was then pressurized with oxygen (3 bar). The reaction mixture was heated to 100 C for 24 h under constant stirring(1000 rpm), then cooled to room temperature and analyzed. 1H-NMR spectroscopy was used for product identification; spectrawere acquired over a 16 scan period using a Bruker 400 MHz DPXsystem with a 5 mm auto tune broadband probe. All samples were prepared as dilute solutions in D2O. Carbon mass balances were calculated and were between 96 and 104percent. Blank reactions have also been carried out with no oxidation activity detected in the absence of catalyst or with the KB-B carbon support.

A: 71 %Spectr. B: 29 %Spectr.

With oxygen in water

T=100°C; P=2250.23 Torr; 24 h; Hide Experimental Procedure

Ryabenkova, Yulia; Miedziak, Peter J.; Knight, David W.; Taylor, Stuart H.; Hutchings, Graham J.

Tetrahedron, 2014 , vol. 70, # 36 p. 6055 - 6058 Title/Abstract Full Text View citing articles Show Details

4.2 Butanediol oxidation

General procedure: (0017) Reactions were carried out using a Radley's low pressure glass reactor (50ml). A butanediol in water (20ml, 0.6M) and the catalyst (butanediol/metal ratio=2000) were added into the reactor, which was then pressurized with oxygen (3bar). The reaction mixture was heated to 100°C for 24h under constant stirring (1000rpm), then cooled to room temperature and analyzed. 1H NMR spectroscopy was used for product identification; spectra were acquired over a 16 scan period using a Bruker 400MHz DPX system with a 5mm auto tune broadband probe. All samples were prepared as dilute solutions in D2O. Carbon mass balances were calculated and were between 96 and 104percent. Blank reactions have also been carried out with no oxidation activity detected in the absence of catalyst or with the KB-B carbon support. A

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De Schouwer, Free; Claes, Laurens; Claes, Nathalie; Bals, Sara; Degrve, Jan; De Vos, Dirk E.

Green Chemistry, 2015 , vol. 17, # 4 p. 2263 - 2270 Title/Abstract Full Text View citing articles Show Details

in water

T=250°C; P=4500.45 Torr; pH=1.8; 6 h; Inert atmosphere; Reagent/catalystTemperaturepH-value; Overall yield = 99 percent;

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With hydrogen in 1,4-dioxane

T=240°C; P=22502.3 - 45004.5 Torr; 2 h; Autoclave;

You, Chenjia; Zhang, Chi; Chen, Lifang; Qi, Zhiwen

Applied Organometallic Chemistry, 2015 , vol. 29, # 10 p. 653 - 660 Title/Abstract Full Text View citing articles Show Details

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With 3-(N-morpholino)propanesulfonic acid; iron sulphate heptahydrate; zinc sulfate heptahydrate powder; potassium dihydrogenphosphate; ((NH4)2HPO4); CuSO4 5H2O; magnesium sulphate heptahydrate; manganese(II) sulfate heptahydrate; (NH4)6[Mo7O24]*4H2O; B4O7(2)*7H O*2Na(1+); calcium chloride

Rx-ID: 41346931 Find similar reactions

Samsung Electronics Co., Ltd.; Lee, Kyunghae; Lee, Mooho; Chwae, Jun; Park, Jinhwan; Lee, Jongmin; Cho, Kwangmyung; Park, Jaechan

Patent: US2015/259311 A1, 2015 ; Location in patent: Paragraph 0031 ; Title/Abstract Full Text Show Details

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Enzymatic reaction; Hide Experimental Procedure

10031] E. Coli producing 4-RB was cultured in a medium (13.5 g KR2PO4, 4 g (NR4)2RP04, 1.7 g citric acid, 1.4 g MgSO4.7R20, Yeast extract 2 g, MOPS 21 g, 10 mE trace metal solution (10 g Fe504.7R20, 1.35 g CaC12, 2.25 g Zn504.7R20, 0.5 g Mn504.4R20, 1 g Cu504.5R20, 0.106 g (NR4)5Mo7O24.4R20, 0.23 gNa2B4O7.10R20, 35percent RC1 10 mE per 1 L distilled water) per 1 L distilled water) for 200 hours to obtain 9-12 (w/v) percent 4-RB containing culture solution (pR about 6.-7.0). 95 (w/v) percent sulthric acid was added to 100 ml of the culture solution so that pR of the culture solutionwas 0.5, 1.0,2.0, or 4.0 in each ofthe 100 ml ofthe culture solution as a sample. The culture solution was maintained at room temperature for 1 hour to allow 4-RB to convert to GBL. After 1 hour, each of the samples was placed in RPLC (Waters, Colunm: C18, Room Temperature (25°C.), UV: 195 nm, Flow: 1.0 ml/min, Injection volume: 2 tL, Buffer: 25 mM KR2PO4) and GC (Younglin G C, Detector: FID) to measure 4-RB and GBL. Table 1 shows the effect of pR on conversion of 4-RB to GBL.

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With 3-(N-morpholino)propanesulfonic acid; thiamine hydrochloride; isopropyl 1-thio-β-D-galactopyranoside in aq. buffer Microbiological reaction; Reagent/catalyst; Hide Experimental Procedure

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Rx-ID: 41650879 Find similar reactions

Genomatica, Inc.; Burk, Mark J.; Burgard, Anthony P.; Osterhout, Robin E.; Sun, Jun

Patent: US9175297 B2, 2015 ; Location in patent: Page/Page column 63-64 ; Title/Abstract Full Text Show Details

II:Production of 4-HB from Glucose.

Production of 4-HB from Glucose. (0241) Although the above experiments demonstrate a functional pathway to 4-HB from a central metabolic intermediate (succinate), an industrial process would require the production of chemicals from low-cost carbohydrate feedstocks such as glucose or sucrose. Thus, the next set of experiments was aimed to determine whether endogenous succinate produced by the cells during growth on glucose could fuel the 4-HB pathway. Cells were grown anaerobically in M9 minimal medium (6.78 g/L Na2HPO4, 3.0 g/L KH2PO4, 0.5 g/L NaCl, 1.0 g/L NH4Cl, 1 mM MgSO4, 0.1 mM CaCl2) supplemented with 20 g/L glucose, 100 mM 3-(N-morpholino)propanesulfonic acid (MOPS) to improve the buffering capacity, 10 μg/mL thiamine, and the appropriate antibiotics. 0.25 mM IPTG was added when OD600 reached approximately 0.2, and samples taken for 4-HB analysis every 24 hours following induction. In all cases 4-HB plateaued after 24 hours, with a maximum of about 1 mM in the best strains (FIG. 3a), while the succinate concentration continued to rise (FIG. 3b). This indicates that the supply of succinate to the pathway is likely not limiting, and that the bottleneck may be in the activity of the enzymes themselves or in NADH availability. 0035 and 0036 are clearly the best gene candidates for CoA-dependent succinic semialdehyde dehydrogenase and 4-HB dehydrogenase, respectively. The elimination of one or both of the genes encoding known (gabD) or putative (aldA) native succinic semialdehyde dehydrogenases had little effect on performance. Finally, it should be noted that the cells grew to a much lower OD in the 4-HB-producing strains than in the controls (FIG. 3c). A

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With 1-(n-butyl)-3-methylimidazolium triflate

T=340°C; 2 h; Inert atmospherePyrolysis; Hide Experimental Procedure

Qu, Guangfei; He, Weiwei; Cai, Yingying; Huang, Xi; Ning, Ping

Carbohydrate Polymers, 2016 , vol. 148, p. 390 - 396 Title/Abstract Full Text View citing articles Show Details

2.3. The pyrolysis of microcrystalline cellulose in [bmim]OTf

General procedure: Flow chart of the experiment is shown in Fig. 1. Nitrogen was used as carrier gas. Gas produced from the reactor was purged with nitrogen into aluminum foil bag. Nitrogen flow was controlled at 5 ml/min by mass flow controller. Used a glass sand at the bottom of the reactor to ensure nitrogen take away gas phase products. 1.000 g microcrystalline cellulose and 10,000 g [bmim]OTf were added into reactor. Nitrogen was kept aerating until the reactor contained no more air but only nitrogen. The reactor is connected to the aluminum foil bags, and then using magnetic stirring for 2 h under the condition of 180°C, 240°C and 340°C, respectively. When pyrolysis reaction finished, close the heating device and aerate moderate amount of nitrogen. The gas phase products are collected under the nitrogen purging aluminum foil sample bag while volatile liquid products are collected in a liquid bottle after the condensation. Deionized water and dichloromethane were added while the reactor was cooled to room temperature, and then the cracking solid products were collected and dried by suction filtration. Liquid products was added into the separatory funnel, after stratification, the lower liquid was evaporated to remove the methylene chloride in order to obtain difficult volatile liquid products.

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With sodium hydroxide in water

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Rx-ID: 10243811 Find similar reactions

Naeser, Ulrike; Pierik, Antonio J.; Scott, Richard; Cinkaya, Irfan; Buckel, Wolfgang; Golding, Bernard T.

Bioorganic Chemistry, 2005 , vol. 33, # 1 p. 53 - 66 Title/Abstract Full Text View citing articles Show Details

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With sodium hydroxide in water

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Rx-ID: 10243812 Find similar reactions

Naeser, Ulrike; Pierik, Antonio J.; Scott, Richard; Cinkaya, Irfan; Buckel, Wolfgang; Golding, Bernard T.

Bioorganic Chemistry, 2005 , vol. 33, # 1 p. 53 - 66 Title/Abstract Full Text View citing articles Show Details

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With sodium hydroxide in water

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Rx-ID: 10243813 Find similar reactions

Naeser, Ulrike; Pierik, Antonio J.; Scott, Richard; Cinkaya, Irfan; Buckel, Wolfgang; Golding, Bernard T.

Bioorganic Chemistry, 2005 , vol. 33, # 1 p. 53 - 66 Title/Abstract Full Text View citing articles Show Details

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With sodium hydroxide in water

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Rx-ID: 10243814 Find similar reactions

Naeser, Ulrike; Pierik, Antonio J.; Scott, Richard; Cinkaya, Irfan; Buckel, Wolfgang; Golding, Bernard T.

Bioorganic Chemistry, 2005 , vol. 33, # 1 p. 53 - 66 Title/Abstract Full Text View citing articles Show Details

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With sodium hydroxide; bromine in 1,4-dioxane

T=15°C; 2 h;

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Rx-ID: 9747483 Find similar reactions

Scott, Richard; Naeser, Ulrike; Friedrich, Peter; Selmer, Thorsten; Buckel, Wolfgang; Golding, Bernard T

Chemical communications (Cambridge, England), 2004 , # 10 p. 1210 - 1211 Title/Abstract Full Text View citing articles Show Details

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With sodium hydroxide; bromine in 1,4-dioxane

T=15°C;

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Rx-ID: 9747484 Find similar reactions

Scott, Richard; Naeser, Ulrike; Friedrich, Peter; Selmer, Thorsten; Buckel, Wolfgang; Golding, Bernard T

Chemical communications (Cambridge, England), 2004 , # 10 p. 1210 - 1211 Title/Abstract Full Text View citing articles Show Details

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With sodium tetrahydroborate in water

T=20°C; 12.5 h;

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Rx-ID: 11161077 Find similar reactions

Wheatley, Bronwen M. M.; Keay, Brian A.

Journal of Organic Chemistry, 2007 , vol. 72, # 19 p. 7253 - 7259 Title/Abstract Full Text View citing articles Show Details

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With sodium hydroxide in water

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Rx-ID: 10243999 Find similar reactions

Naeser, Ulrike; Pierik, Antonio J.; Scott, Richard; Cinkaya, Irfan; Buckel, Wolfgang; Golding, Bernard T.

Bioorganic Chemistry, 2005 , vol. 33, # 1 p. 53 - 66 Title/Abstract Full Text View citing articles Show Details

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100%

With lithium hydroxide monohydrate in methanol; water

T=20°C; 16 h; Hide Experimental Procedure

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Rx-ID: 10672197 Find similar reactions

ACTELION PHARMACEUTICALS LTD; GUDE, Markus; HUBSCHWERLEN, Christian; PANCHAUD, Philippe

Patent: WO2012/131588 A1, 2012 ; Location in patent: Page/Page column 137 ; Title/Abstract Full Text Show Details

90.1:

90.1. Lithium 4-hydroxybutanoate:To a solution of γ-butyrolactone (170 mg) in MeOH (0.5 mL) were added water (0.2 mL) and lithium hydroxide monohydrate (83 mg). The reaction mixture was stirred at rt for 16 h and concentrated under reduced pressure. The title compound was obtained, without additional purification, as a white solid (243 mg; quantitative yield).

100%

With lithium hydroxide in methanol; water

T=20°C; 16 h;

QUANTICEL PHARMACEUTICALS, INC; NIE, Zhe; STAFFORD, Jeffrey, Alan; VEAL, James, Marvin; WALLACE, Michael, Brennan

Patent: WO2014/89364 A1, 2014 ;

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Location in patent: Paragraph 00763; 00764 ; Title/Abstract Full Text Show Details

8.A:A. 4-hydroxybutanoyloxylithium

A. 4-hydroxybutanoyloxylithium [00764] Charge oxolan-2-one (9.64 g, 0.11 mmol), lithium hydroxide (4.7g, 0.11 mmol), methanol (10 mL) and water (4 mL) to a flask. The reaction mixture was stirred at r.t. for 16 h. The solvent was removed to give the title compound (14.1g, 100percent) which was used for the next step without further purification.

With lithium hydroxide; water in methanol

T=20°C; Hide Experimental Procedure

Long, Daniel D.; Church, Timothy J.; Jacobsen, John R.; Jiang, Lan; Saito, Daisuke Roland; Stergiades, Ioanna; Van Dyke, Priscilla M.; Dalziel, Sean; Preza, Leticia Maria

Patent: US2007/219278 A1, 2007 ; Location in patent: Page/Page column 40 ; Title/Abstract Full Text Show Details

98:

To a solution of γ-butyrolactone (170.0 mg, 1.98 mmol) in methanol (0.5 mL) was added water (0.2 mL) and lithium hydroxide monohydrate (83 mg, 2.0 mmol). The resulting mixture was stirred at room temperature overnight. After concentration, the residue was dried over the vacuum line to give the intermediate, lithium 4-hydroxybutyrate as a white solid. The intermediate (18.3 mg, 0.17 mmol) was added to a mixture of 3-endo-{8-[2-(cyclohexylmethylamino)ethyl]-8-azabicyclo[3.2.1]oct-3-yl}benzamide bis TFA salt (50 mg, 0.083 mmol) and DIPEA (58.3 μL, 0.33 mmol) in DMF (0.4 mL). Then HATU (63.1 mg, 0.17 mmol) was added and the resulting reaction mixture was stirred at room temperature overnight. After concentration, the residue was redissolved in 50percent acetic acid in water (6 mL), filtered and purified by preparative HPLC. Desired fractions were combined and freeze dried to give a white solid. 1H NMR (CD3OD, 400 MHz) δ (ppm): 8.05(s, 1H), 7.79(d, J=8.0 Hz, 1H), 7.74(d, J=7.6 Hz, 1H), 7.51(dd, J=7.6, 8.0 Hz, 1H), 4.13(brs, 2H), 3.78(t, J=5.6 Hz, 2H), 3.69(t, J=6.0 Hz, 2H), 3.31-3.35(obscure 3H, overlap with solvent), 3.17(t, J=5.6 Hz, 2H), 2.43-2.53(m, 6H), 2.01-

2.05(m, 2H), 1.61-1.84(m, 10H), 1.12-1.26(m, 3H), 0.89-0.98(m, 2H). (m/z): [M+H]+ calcd for C27H41N3O3 456.31; found 456.4. A

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With recombinant escherichia coli BL21(DE3) expressing alcohol dehydrogenase from micrococcus luteus NCTC2665, Baeyer–Villiger monooxygenase from pseudomonas putida KT2440 in aq. buffer T=35°C; pH=8; Microbiological reaction; Overall yield = > 60 percent;

Song, Ji-Won; Jeon, Eun-Yeong; Song, Da-Hyun; Jang, Hyun-Young; Bornscheuer, Uwe T.; Oh, Deok-Kun; Park, Jin-Byung

Angewandte Chemie - International Edition, 2013 , vol. 52, # 9 p. 2534 - 2537 Angew. Chem., 2013 , vol. 125, # 9 p. 2594 - 2597,4 Title/Abstract Full Text View citing articles Show Details

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A: 0.77% B: 0.38% C: 0.24% D: 0.05% E: 98.28% F: 0.02% G: 0.26%

With hydrogen; 0.5percent Pd on Rutile TiO2

T=110°C; Product distribution / selectivity; Hide Experimental Procedure

Bhattacharyya, Alakananda; Manila, Maynard D.

Patent: US2006/4212 A1, 2006 ; Location in patent: Page/Page column 18-19 ; Title/Abstract Full Text Show Details

1st-Stage Material 10 0.5percent Pd on 1/16 Rutile Catalvst Preparation Materials: Rutile TiO2 Support (94percent Rutile, 6percent Anatase 1/16 inch (1.5 mm) diameter) Titanium dioxide containing 96 wt percent of the rutile crystalline phase of titanium dioxide and 6 wt percent of the anatase crystalline phase of titanium dioxide, 49.5 g (dry). Pd Impregnation Solution 1.31 g of Pd (NO3)2 Solution (19.02 wt percent Pd) is mixed with 6.12 g concentrated nitric acid (70percent nitric acid). This solution is used to impregnate the 96percent rutile titanium dioxide support. Preparation Procedure: Step 1

The 96percent rutile titanium dioxide support is gradually impregnated with the Pd impregnation solution, and allowed to stand for 1 hr. The material is then dried in an oven at 130° C. for 3.5 hr. 2nd-Stage Material Carbon Catalyst-Aqueous Two-step Preparation of BDO Catalyst with 1.5 mm Carbon Support This procedure describes an aqueous two-step BDO catalyst preparation using Norit 1.5 mm carbon. Nominal Composition: 0.4percent Fe, 1.9percent Na, 2.66percent Ag, 2.66percent Pd, 1 0.0percent Re on 1.5 mm diameter carbon. Materials: (A) Carbon Support: 58.4 g of Norit 1.5 mm diameter Active Carbon extrudate (referred to herein as Standard C or standard carbon) (acquired from Norit Americas Inc. located in Atlanta, Ga.) (B) Ag/Fe/Na Impregnation Solution: 2.9 g of silver nitrate, 5.1 g of sodium nitrate and 2 g of [Fe(NO3)3.9H2O] are dissolved in 20 g of de-ionized water and then gradually mixed with 68.3 g of concentrated nitric acid (70 wt percent nitric acid). (C) Pd/Re Impregnation Solution 1: 9.1 g of Pd (NO3)2 solution (20.38percent Pd), 12.22 g of HReO4 solution (56.36 wt percent Re), 23.3 g of concentrated nitric acid (70 wt percent nitric acid), and 24 g of deionized water are mixed together. Preparation Procedure: Step 1 The carbon support (A) is gradually impregnated with the Ag/Fe/Na impregnation solution (B), and allowed to stand for 1 hr. The material is then dried in an oven at 130° C. for 4.5 hr. Step 2 The carbon support (A) which has been impregnated with Ag/Fe/Na is next gradually impregnated with the Pd/Re solution (C) and the mixture is allowed to stand for 3 hr. The catalyst is then dried for 5 hr at 130° C. The rutile titanium dioxide support is gradually impregnated with the Pd/Re impregnation solution, and allowed to stand for 1 hr. The material is then dried in an oven at 130° C. for 3.5 hr. A

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With oxygen in water

T=100°C; P=2250.23 Torr; 24 h; Reagent/catalyst; Hide Experimental Procedure

Ryabenkova, Yulia; Miedziak, Peter J.; Knight, David W.; Taylor, Stuart H.; Hutchings, Graham J.

Tetrahedron, 2014 , # 36 p. 6055 - 6058 Title/Abstract Full Text Show Details

Butanediol oxidation

A: 76 %Spectr. B: 18 %Spectr. C: 6 %Spectr.

With oxygen in water

T=100°C; P=2250.23 Torr; 24 h; Hide Experimental Procedure

Ryabenkova, Yulia; Miedziak, Peter J.; Knight, David W.; Taylor, Stuart H.; Hutchings, Graham J.

Tetrahedron, 2014 , vol. 70, # 36 p. 6055 - 6058 Title/Abstract Full Text View citing articles Show Details

4.2 Butanediol oxidation

A: 63 %Spectr. B: 21 %Spectr. C: 16 %Spectr.

With oxygen in water

T=100°C; P=2250.23 Torr; 24 h; Hide Experimental Procedure

Ryabenkova, Yulia; Miedziak, Peter J.; Knight, David W.; Taylor, Stuart H.; Hutchings, Graham J.

Tetrahedron, 2014 , vol. 70, # 36 p. 6055 - 6058 Title/Abstract Full Text View citing articles Show Details

4.2 Butanediol oxidation

A: 66 %Spectr. B: 23 %Spectr. C: 11 %Spectr.

With oxygen in water

T=100°C; P=2250.23 Torr; 24 h;

Ryabenkova, Yulia; Miedziak, Peter J.; Knight, David W.; Taylor, Stuart H.; Hutchings, Graham J.

Tetrahedron, 2014 , vol. 70, # 36 p. 6055 - 6058 Title/Abstract Full Text View citing articles Show Details

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B: 80 %Spectr.

With Oxonereg;; cobalt(II)(tetrafluoroborate)2 hexahydrate in water-d2

T=25°C; 0.666667 h;

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Sinha, Shashi Bhushan; Campos, Jess; Brudvig, Gary W.; Crabtree, Robert H.

RSC Advances, 2014 , vol. 4, # 90 p. 49395 - 49399 Title/Abstract Full Text View citing articles Show Details

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With sodium hydroxide

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Rx-ID: 360152 Find similar reactions

Nelson; Cretcher

Journal of the American Chemical Society, 1930 , vol. 52, p. 3702 Full Text View citing articles Show Details

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Rx-ID: 1522666 Find similar reactions

95%

With ethanol; sodium hydroxide

T=20°C; 2 h;

Rival, Nicolas; Hazelard, Damien; Hanquet, Gilles; Kreuzer, Thomas; Bensoussan, Charlelie; Reymond, Sébastien; Cossy, Janine; Colobert, Françoise

Organic and Biomolecular Chemistry, 2012 , vol. 10, # 47 p. 9418 - 9428 Title/Abstract Full Text View citing articles Show Details

89%

With sodium hydroxide in ethanol; water

Reflux; Hide Experimental Procedure

ONYX THERAPEUTICS, INC.; MCMINN, Dustin; JOHNSON, Henry; MOEBIUS, David, C.

Patent: WO2014/152127 A1, 2014 ; Location in patent: Paragraph 00340; 00341 ; Title/Abstract Full Text Show Details

15:Benzyl 4-hydroxybutanoate

To a solution of dihydrofuran-2(3H)-one (20.0 g, 23.3 mmol) in ethanol (200 mL) were added water (100 ml) and sodium hydroxide (9.3 g, 233 mmol). The reaction mixture was heated under reflux overnight. The mixture was concentrated and the residue was washed with THF/EtOH (1 : 1, 100 mL) to afford sodium 4-hydroxy butanoate (26.1 g, 89percent yield) as a white solid

85%

With sodium trimethylsilanolate in dichloromethane

T=20°C; 4 h; Inert atmosphere; SolventTime; chemoselective reaction;

Lemoine, Hugues; Marković, Dean; Deguin, Brigitte

Journal of Organic Chemistry, 2014 , vol. 79, # 10 p. 4358 - 4366 Title/Abstract Full Text View citing articles Show Details

Hide Details

81%

With water; sodium hydroxide in ethanol

5 h; Reflux;

Smeenk, Linde E. J.; Dailly, Nicolas; Hiemstra, Henk; Van Maarseveen, Jan H.; Timmerman, Peter

Organic Letters, 2012 , vol. 14, # 5 p. 1194 - 1197 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide in water

T=70°C;

Weber; Halgren; Doyle; Lynch; Siegl; Parsons; Greenlee; Patchett

Journal of Medicinal Chemistry, 1991 , vol. 34, # 9 p. 2692 - 2701 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide in methanol

5 h; Heating;

Goto; Okamoto; Okutani; Imada

Chemical and Pharmaceutical Bulletin, 1985 , vol. 33, # 10 p. 4422 - 4431 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide in water

NORAC, INC.

Patent: WO2009/129350 A2, 2009 ; Location in patent: Page/Page column 22-24 ;

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Title/Abstract Full Text Show Details

PREPARATION OF ONE-KILOGRAM OF NAGHB AS AN AQUEOUS CONCENTRATE .; [054] The procedure described below was used to prepare a one- kilogram sample of NaGHB as an aqueous concentrate.[055] The following solutions were prepared as feedstock for the continuous reactor: GBL Feedstock Solution - GBL (751.0 g, about 670.5 mL, 8.723 mol) was diluted to 1200 mL with reagent grade water and mixed until homogeneous (clear, colorless); NaOH Feedstock Solution - NaOH (51 wtpercent in H20, 677.4 g, about 447.1 mL, 8.637 mol, 0.99 <n="24"/>equiv) was diluted to 1200 mL with reagent grade water and mixed until homogeneous (clear, colorless) .[056] Both feed solutions were fed through a peristaltic pump at equal flow rates of 21 ml/min through 1.6 mm ID tubing. The two feed solutions were then combined through a union into a 24-inch long static mixing device {PP/LDPE, ID = 8 mm) at a total combined feed rate of 42 ml/min. In this particular instance, a helical-type static mixer within a tube is used, but other static or dynamic mixing devices, including high-shear mixing devices, would be equally effective. The intimately mixed solutions from the outlet of the static mixer are then fed through a 36-inch long tube (PTFE, ID = 3/16") and into a glass receiving vessel .

With water; sodium hydroxide

T=40 - 47.5°C; pH=7.3 - 12; Industry scaleInert atmosphere; Product distribution / selectivity; Hide Experimental Procedure

Title/Abstract Full Text Show Details

Example 1; The continuous process procedure described below is used to prepare a five kilogram sample of sodium γ-hydroxybutyrate as an aqueous concentrate.The following solutions are prepared as feedstock for the continuous reactor: γ-butyrolactone feedstock solution-γ-butyrolactone (3.4 kg, about 3.0 L, 39.4 mol) is diluted with 3.0 L of reagent grade water and mixed until homogeneous (clear, colorless) resulting in a 6.56 M solution of γ-butyrolactone in water; NaOH feedstock solution-NaOH (49 wt percent in H2O, 3.2 kg, about 2.1 L, 39.4 mol, 1.0 equivalent relative to γ-butyrolactone) is diluted with 4.2 L of reagent grade water, mixed until homogeneous (clear, colorless), and allowed to cool to room temperature, resulting in a 6.56 M solution of NaOH in water. The headspace above both feedstock solutions is kept inert under a blanket of nitrogen during preparation and reaction.Each solution is fed by peristaltic pump through separate jacketed (Tjacket=0° C.) static mixers (316SS, 21 alternating split-helical mixing elements, 0.25 OD.x.0.194 ID.x.11.50 L) to pre-cool the feed solutions prior to mixing. The aqueous γ-butyrolactone solution is fed at a set flow rate of about 52.0 mL/min, while the aqueous NaOH solution is fed at a slightly lower flow rate of about 49.5 mL/min. The two pre-cooled feed solutions are combined through a union and fed concurrently into two jacketed static mixers (316SS, 32 alternating split-helical mixing elements, 0.50 OD.x.0.43 ID.x.24.75 L) in series at a total combined feed rate of about 101.5 mL/min. As the two feed solutions are of equivalent concentration, these flow rates result in a reaction ratio of 0.95 equivalents of NaOH relative to γ-butyrolactone in the reactor. The fluid in the first reactor jacket in the series is maintained at 25° C.+/-2.5° C. (concurrent flow) while the fluid in the second is maintained at 55° C.+/-2.5° C. (countercurrent flow). For the reactor and reaction conditions described above, the pH of process stream immediately after the first jacketed reactor is typically 12+/-0.5 at a temperature of 40+/-2.5° C., while the pH of the process stream immediately after the second jacketed reactor is typically 10+/-1.0 at a temperature of 47.5+/-2.5° C. The intimately mixed solutions from the outlet of the reactor are fed through a tube (polypropylene, 0.25 OD, 0.125 ID) and collected in a receiving vessel. The headspace above the product solution is kept inert under a blanket of nitrogen during and after the reaction. The pH of the resulting clear, colorless to straw yellow solution, at equilibrium, is typically 7.3+/-0.1.The relative ratio of the reagants in the reaction zone in this Example is determined by the following calculation, using equations (1) and (2) discussed above.The solution is then concentrated in vacuo using a Wiped-Film Evaporator (WFE) to a sodium γ-hydroxybutyrate aqueous concentrate of about 40 wt percent to about 55 wt percent. The headspace above the feed and product solutions for the WFE are kept inert under a blanket of nitrogen during concentration.The sodium γ-hydroxybutyrate aqueous concentrate is then filtered (10-20 micron filter) and packaged. The headspace above the feed and product solutions for the filtration and packaging operations are kept inert under a blanket of nitrogen. After concentration, the pH of the solution is typically 7.7+/-0.1 (upon reaching equilibrium). In this instance, equilibrium is reaching during the concentration process. The resulting aqueous concentrate meets or exceeds 99percent purity as measured by GC analysis of the bis-TMS (trimethylsilyl) derivative of the final product.

With sodium hydroxide in ethanol

T=70°C;

Zhai, Duanting; Tan, Yong Qiao Elton; Xu, Wang; Chang, Young-Tae

Chemical Communications, 2014 , vol. 50, # 22 p. 2904 - 2906 Title/Abstract Full Text View citing articles Show Details

With sodium hydroxide in water; toluene

PTM Biolabs, Inc.; Zhao, Yingming; Xie, Zhongyu

Patent: US2015/51093 A1, 2015 ; Location in patent: Page/Page column ;

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Luchi, James; Levin, Daniel

Patent: US2011/34727 A1, 2011 ; Location in patent: Page/Page column 5 ;

Title/Abstract Full Text Show Details

1:Materials and Methods

Fmoc-Lys(4-(tritylO) butyryl)-OH. Step 1: A mixture of 2.58 g (30 mM, 2.28 mL) of 4-butyrolactone and 1.2 g (30 mM) of sodium hydroxide in 30 mL of water was heated at 70° C. overnight. The clear solution was cooled and concentrated. The resulting white solid was suspended in toluene and concentrated further to remove the remaining trace amounts of water. An almost quantitative yield of sodium 4-hydroxybutyrate was obtained.

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With methanol-d1; sodium hydroxide

Hide Experimental Procedure

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Rx-ID: 29871489 Find similar reactions

CONCERT PHARMACEUTICALS, INC.; TUNG, Roger, D.

Patent: WO2010/124046 A1, 2010 ; Location in patent: Page/Page column 28 ; Title/Abstract Full Text Show Details

Example 1. Sodium 2.2-d2-4-hvdroxybutyrate.Sodium 2,2-d2-4-hydroxybutyrate is prepared in the following manner: treatment of succinic anhydride with tert-butanol, N-hydroxysuccinimide, and A- dimethylaminopyridine (4-DMAP) according to the procedure of Yao, Z-J., et al, J. Org. Chem. 2003, 68, 6679-6684 affords the succinic acid mono-tert-butyl ester. In accordance with Yao, reduction of the succinic acid with borane-dimethyl sulfide complex gives the 4-hydroxybutanoic acid tert-butyl ester. Subjecting the ester to hydrogen/deuterium exchange by treatment with potassium carbonate in dl methanol affords the 2,2-d2 -4-hydroxybutanoic acid tert-butyl ester. Finally, saponification of the tert-butyl ester with sodium hydroxide in dl -methanol in a manner analogous to the procedure of Goto, G., et al, Chem. Pharm. Bull. 1985, 33, 4422-4431 affords the desired sodium 2,2-d2-4-hydroxybutyrate.

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92%

With methanol; sodium hydroxide

5 h; Reflux; Hide Experimental Procedure

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Rx-ID: 29871491 Find similar reactions

CONCERT PHARMACEUTICALS INC.; TUNG, Roger, D.; MORGAN, Adam; SILVERMAN, I., Robert

Patent: WO2012/112492 A1, 2012 ; Location in patent: Page/Page column 43 ; Title/Abstract Full Text Show Details

2.3:

Step 3. Sodium 3,3-dp-4-hvdroxybutanoate: To a solution of 2 (2.06 g, 23.4 mmol) in methanol (100 mL) was added solid sodium hydroxide (918 mg, 22.9 mmol). The reaction stirred at reflux for 5 hours then was concentrated under reduced pressure to afford sodium 3,3-dideutero-4-hydroxybutanoate as a white solid (2.75 g, 92percent). H NMR (CDCI3, 400 MHz) δ 6.17 (s, 1 H), 3.38 (s, 2H), 2.01 (s, 2H).

92%

With methanol; sodium hydroxide

15 h; Reflux; Hide Experimental Procedure

CONCERT PHARMACEUTICALS, INC.; TUNG, Roger D.; SILVERMAN, I. Robert

Patent: WO2014/31840 A1, 2014 ; Location in patent: Paragraph 187 ; Title/Abstract Full Text Show Details

2.3:Step 3. Sodium 3.3-dp-4-hvdroxybutanoate

To a solution of 2 (2.06 g, 23.4 mmol) in methanol (100 ml_) was added solid sodium hydroxide (918 mg, 22.9 mmol). The reaction stirred at reflux for 5 hours then was concentrated under reduced pressure to afford sodium 3,3-dideutero-4-hydroxybutanoate as a white solid (2.75 g, 92percent). H NMR (CDCI3, 400 MHz) δ 6.17 (s, 1 H), 3.38 (s, 2H), 2.01 (s, 2H).

With methanol-d1; sodium hydroxide

Hide Experimental Procedure

CONCERT PHARMACEUTICALS, INC.; TUNG, Roger, D.

Patent: WO2010/124046 A1, 2010 ; Location in patent: Page/Page column 28-29 ; Title/Abstract Full Text Show Details

Example 2. Sodium 3,3-d2-4-hydroxybutyrateSodium 3,3-d2-4-hydroxybutyrate is prepared in the following manner: treatment of mono-methylsuccinate with sodium methoxide in dl -methanol in a manner analogous to the procedure of Keay, B. A., et al, J. Org. Chem. 2007, 72, 7253-7259 affords the butanedioic-2,2-d2 acid, 1 -methyl ester. Treatment of the d2 ester in a manner analogous to Keay et al. with sodium borohydride in water affords the 4,4-dideutero- dihydrofuran-2(3H)-one. Finally, saponification of the dideutro-butyrolactone with sodium hydroxide in dl-methanol in a manner

analogous to the procedure of Goto, G., et al, Chem. Pharm. Bull. 1985, 33, 4422-4431 affords the desired sodium 3,3-d2-4- hydroxybutyrate .

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88%

Rx-ID: 33820573 Find similar reactions

CONCERT PHARMACEUTICALS INC.; TUNG, Roger, D.; MORGAN, Adam; SILVERMAN, I., Robert

Patent: WO2012/112492 A1, 2012 ; Location in patent: Page/Page column 41-42 ;

Title/Abstract Full Text Show Details

88%

With methanol; sodium hydroxide

15 h; Reflux; Hide Experimental Procedure

CONCERT PHARMACEUTICALS, INC.; TUNG, Roger D.; SILVERMAN, I. Robert

Patent: WO2014/31840 A1, 2014 ; Location in patent: Paragraph 183; 187 ; Title/Abstract Full Text Show Details

1.2:Step 3. Sodium 3.3-dp-4-hvdroxybutanoate

General procedure: To a solution of 2 (2.06 g, 23.4 mmol) in methanol (100 ml_) was added solid sodium hydroxide (918 mg, 22.9 mmol). The reaction stirred at reflux for 5 hours then was concentrated under reduced pressure to afford sodium 3,3-dideutero-4-hydroxybutanoate as a white solid (2.75 g, 92percent). H NMR (CDCI3, 400 MHz) δ 6.17 (s, 1 H), 3.38 (s, 2H), 2.01 (s, 2H).

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With methanol-d1; sodium hydroxide

Hide Experimental Procedure

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Rx-ID: 29871493 Find similar reactions

CONCERT PHARMACEUTICALS, INC.; TUNG, Roger, D.

Patent: WO2010/124046 A1, 2010 ; Location in patent: Page/Page column 29 ; Title/Abstract Full Text Show Details

Sodium 2.2.3.3-d4-4-hvdroxybutyrateSodium 2,2,3,3-d4-4-hydroxybutyrate is prepared in the following manner: treatment of 3,3,4,4-d4-tetrahydrofuran with calcium hypochlorite in acetonitrile according to the procedure of de Meijere, A. et al., Chem. Eur. J. 2007, 13, 167-177 affords the 3,3,4,4- tetradeutero-dihydrofuran-2(3H)-one. Saponification of the tetradeutero-butyrolactone with sodium hydroxide in dl-methanol in a manner analogous to the procedure of Goto, G., et al, Chem. Pharm. Bull. 1985, 33, 4422-4431 affords the desired sodium 2,2,3,3- d4-4-hydroxybutyrate .

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89%

Rx-ID: 33820571 Find similar reactions

CONCERT PHARMACEUTICALS INC.; TUNG, Roger, D.; MORGAN, Adam; SILVERMAN, I., Robert

Patent: WO2012/112492 A1, 2012 ; Location in patent: Page/Page column 44 ;

Title/Abstract Full Text Show Details

89%

With methanol; sodium hydroxide

15 h; Reflux; Hide Experimental Procedure

CONCERT PHARMACEUTICALS, INC.; TUNG, Roger D.; SILVERMAN, I. Robert

Patent: WO2014/31840 A1, 2014 ; Location in patent: Paragraph 187; 191 ; Title/Abstract Full Text Show Details

3.3:Step 3. Sodium 3.3-dp-4-hvdroxybutanoate

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85%

Rx-ID: 33820574 Find similar reactions

CONCERT PHARMACEUTICALS INC.; TUNG, Roger, D.; MORGAN, Adam; SILVERMAN, I., Robert

Patent: WO2012/112492 A1, 2012 ; Location in patent: Page/Page column 45 ; Title/Abstract Full Text Show Details

85%

With methanol; sodium hydroxide

15 h; Reflux; Hide Experimental Procedure

CONCERT PHARMACEUTICALS, INC.; TUNG, Roger D.; SILVERMAN, I. Robert

Patent: WO2014/31840 A1, 2014 ; Location in patent: Paragraph 187; 195 ; Title/Abstract Full Text Show Details

4.3:Step 3. Sodium 3.3-dp-4-hvdroxybutanoate

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A: 1.27% B: 4.78% C: 1.55% D: 1.24% E: 0.48% F: 90.6% G: 0.08%

With hydrogen; 0.5percent Pd/2.0percent Re on Rutile TiO2

T=110°C; Product distribution / selectivity; Hide Experimental Procedure

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Bhattacharyya, Alakananda; Manila, Maynard D.

Patent: US2006/4212 A1, 2006 ; Location in patent: Page/Page column 11-13 ; Title/Abstract Full Text Show Details

The catalyst testing unit is comprised of a two-reactor system connected in series where maleic acid is first converted to succinic acid (SAC) in the first reactor at about 110° C. The effluent from the first stage reactor is delivered to the second stage reactor for the conversion of succinic acid to mainly BDO. Operating pressure is at 2500 to 4000 psi and internal reactor temperature is initially set at 165° C. Thereafter, temperature is adjusted closer to the temperature where a high conversion of SAC (about 99.7percent) is obtained. This temperature generally may vary from about 130° C. to about 175° C. At the lower end of the temperature range BDO selectivity is higher (80percent or higher) whereas THF is favored at higher temperatures (over 5percent). The results of the activity evaluation of a catalysts made according to the procedure of catalyst Example 1(a) is shown in Table 1a. Activity evaluation of a catalyst made according to the procedure of catalyst Example 2 is shown in Table 1(b). Catalyst results of the activity evaluation of a catalysts made according to the procedure of catalyst Example 3 is shown in Table 1(c).Tables 1a, 1b and 1c show that catalysts of Example 1(a), comprising Pd/Re on a rutile titanium dioxide support, and catalysts of Example 2 and Example 3, comprising Pd on a rutile titanium dioxide support, completely convert maleic acid to succinic acid with high selectivity to succinic acid and low amounts of other by-products. The Catalyst Testing Unit (CTU) results for Catalyst Example 1 and Catalyst Example 2 show that (a) Both 1/16 inch and inch Rutile extrudates can be used for hydrogenation. For carbon, inch was found to be less effective. (b) For maleic to succinic hydrogenation there is no need for other co-catalysts such as Ag, Fe, Na, etc., (c) 0.5percent Pd alone on a rutile TiO2 support gives good conversion of maleic acid to succinic acid.

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With methanol; potassium hydroxide

T=20 - 25°C; 4.5 h; Hide Experimental Procedure

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Rx-ID: 23488465 Find similar reactions

NICOX S.A.

Patent: WO2005/54175 A2, 2005 ; Location in patent: Page/Page column 6; 7 ; Title/Abstract Full Text Show Details

A solution of gamma butyrolactone (2 g, 23.3 mmol) in methanol (5 ml) was added dropwise to a potassium hydroxide (1.28 g, 22.9 mmol) solution in methanol (10 ml) kept at 25 C by external cooling. The solution was kept at room temperature for 4 h 30 min. The solvent was removed in vacuo until yellow solid residue. The solid was washed with Et2O and dried under reduced pressure. The product was obtained as a yellowish solid (3.25 g). Analyses: MS (ESI neg): 103 (M-); IR (KBr)cm-1: 2958, 1653, 1562 (C=O), 1403,1305, 1059 A

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Rx-ID: 38748913 Find similar reactions

With sodium bis(hydrogen periodato)argentate(III); potassium hydroxide

Kinetics;

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Zhang, Jiong; Huo, Shuying; Shi, Hongmei; Shen, Shigang; Shang, Yanli

Transition Metal Chemistry, 2013 , vol. 38, # 1 p. 15 - 20 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 29627446 Find similar reactions

With NH4Br

T=250°C; P=3750.38 Torr; 5.33333 h; Inert atmosphereAutoclave;

Lammens, Tijs M.; Franssen, Maurice C. R.; Scott, Elinor L.; Sanders, Johan P. M.

Green Chemistry, 2010 , vol. 12, # 8 p. 1430 - 1436 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 23659043 Find similar reactions

A: 0.86% B: 4.34% C: 0.28% D: 1.24% E: 0% F: 85.51%

With hydrogen; 0.5percent Pd/0.2percent Re on Rutile TiO2

T=110°C; 170 - 1009 h; Product distribution / selectivity; Hide Experimental Procedure

Bhattacharyya, Alakananda; Manila, Maynard D.

Patent: US2006/4212 A1, 2006 ; Location in patent: Page/Page column 13 ; Title/Abstract Full Text Show Details

G: 0% H: 0.04% I: 0% J: 0%

Tables 2a and 2b show the results of hydrogenation of maleic acid to succinic acid over several sample time periods using catalysts prepared as described in Catalyst Example 1(a) and Catalyst Example 2. A

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Synthesize Find similar Rx-ID: 42425228 Find similar reactions

With 1-(n-butyl)-3-methylimidazolium triflate

T=240°C; 2 h; Inert atmospherePyrolysis; Hide Experimental Procedure

Qu, Guangfei; He, Weiwei; Cai, Yingying; Huang, Xi; Ning, Ping

Carbohydrate Polymers, 2016 , vol. 148, p. 390 - 396 Title/Abstract Full Text View citing articles Show Details

2.3. The pyrolysis of microcrystalline cellulose in [bmim]OTf

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Rx-ID: 27250351 Find similar reactions

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Hassan, Abdi; Wang, Suning

Journal of the Chemical Society - Dalton Transactions, 1997 , # 12 p. 2009 - 2017 Title/Abstract Full Text View citing articles Show Details

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Synthesize Find similar Rx-ID: 43933943 Find similar reactions

With dihydrogen peroxide

pH=3; Kinetics; Reagent/catalystConcentrationpH-value;

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Rahmani, Amir; Khataee, Alireza; Kaymak, Baris; Vahid, Behrouz; Fathinia, Mehrangiz; Dindarsafa, Mahsa

RSC Advances, 2016 , vol. 6, # 84 p. 81219 - 81230 Title/Abstract Full Text Show Details

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