Query Query Cl H
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10 reactions in Reaxys
2016-06-10 04h:50m:44s (EST)
H NH 2 O
O
Search as: As drawn
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O HO HO
H
HN
NH 2
H
O
Cl
O
H
O
O
Rx-ID: 39677908 View in Reaxys 1/10 Yield 76 %
Conditions & References B-209.a :To a solution of(S)-2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoic acid(2 g, 8.65 mmol) in dryMethanol(20 mL) under N2 atmosphere at 0° C. was addedSOCl2(6.31 mL, 86 mmol) dropwise. After addition the reaction was heated to 80° C. for 8 hours. The volatile component was removed in vacuo, and the residue was co-evaporated with drydiethyl ether(3×5 mL). The resulting salt was exposed to high vacuum to afford(S)-methyl 2-amino-3,3dimethylbutanoate hydrochloride(1.2 g,76percent) asbrownsolid which was submitted for next step without purification.1H NMR (DMSO-D6, δ=2.50 ppm, 400 MHz): δ 8.75 (br. s., 2H), 3.83 (s, 3H), 3.18 (br. s., 1H), 1.02 (s, 9H). With thionyl chloride, Time= 8h, T= 0 - 80 °C , Inert atmosphere Patent; Hewawasam, Piyasena; Lopez, Omar D.; Tu, Yong; Wang, Alan Xiangdong; Xu, Ningning; Kadow, John F.; Meanwell, Nicholas A.; Gupta, Samayamuthula Venkata Satya Arun Kumar; Kumar, Indasi J. Gopi; Ponugupati, Suresh Kumar; Belema, Makonen; US2015/23913; (2015); (A1) English View in Reaxys
76 %
B-209.a :To a solution of (S)-2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoic acid (2 g, 8.65 mmol) in dry Methanol (20mL) under N2 atmosphere at 0°C was added SOCI2(6.31 mL, 86 mmol) dropwise. After addition the reaction was heated to 80°C for 8 hours. The volatile component was removed in vacuo, and the residue was co-evaporated with dry diethyl ether (3 x 5 mL). The resulting salt was exposed to high vacuum to afford (S)-methyl 2-amino-3,3dimethylbutanoate hydrochloride (1.2g,76percent)as brown solid which was submitted for next step without purification.XH NMR (DMSO-D6, δ = 2.50 ppm, 400 MHz): δ 8.75 (br. s., 2 H), 3.83 (s, 3 H), 3.18 (br. s., 1H), 1.02 (s, 9 H). With thionyl chloride, Time= 8h, T= 80 °C Patent; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); (A1) English View in Reaxys
H
NH 2
HO
OH Cl
H
NH 2 O
H
O
Cl
H
O
Rx-ID: 36274776 View in Reaxys 2/10 Yield
Conditions & References 4.1.1 General experimental procedure for synthesis of amino acids esters hydrochlorides 2 General procedure: For the synthesis of compounds 2a, 2c–2g, we used slightly modificated known procedure [1]. To a stirred solution of amino acid (32.2mmol) in dry methanol (100mL) was added drop-wise thionyl chloride (64.4mmol). The temperature was kept between−10 and−5°C. After complete addition, the reaction was stirred at RT overnight. After 16h, the solution was evaporated to dryness. The product was diluted with EtOAc and collected by filtration. The residue was dried under reduced pressure to give an amino acid methyl ester hydrochloride as white crystalline powder. The yields were higher in all experiments than 80percent. Melting point and 1H as well as 13C NMR spectra in D2O were used for characterization of the prepared compounds. The data are in good agreement with literature data [20]. With thionyl chloride, Time= 16h, T= -10 - 20 °C Imramovsky, Ales; Jorda, Radek; Pauk, Karel; Reznickova, Eva; Dusek, Jan; Hanusek, Jiri; Krystof, Vladimir; European Journal of Medicinal Chemistry; vol. 68; (2013); p. 253 - 259 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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O
HO
H 2N
OH
H
NH 2
H
O
Cl
H
O
Rx-ID: 1578098 View in Reaxys 3/10 Yield
Conditions & References
98 %
With hydrochlorid acid, Ambient temperature Griesbeck, Axel G.; Mauder, Harald; Angewandte Chemie; vol. 104; nb. 1; (1992); p. 97 - 99 View in Reaxys With hydrochlorid acid, Ambient temperature, Yield given Griesbeck, Axel G.; Mauder, Harald; Mueller, Ingrid; Chemische Berichte; vol. 125; nb. 11; (1992); p. 2467 - 2476 View in Reaxys With thionyl chloride, Time= 3h, T= 40 °C Wu, Shao-Yong; Hirashima, Akinori; Kuwano, Eiichi; Eto, Morifusa; Agricultural and Biological Chemistry; vol. 51; nb. 2; (1987); p. 537 - 548 View in Reaxys With sulfuryl chloride Thomson, Jennifer E.; Campbell, Craig D.; Concellon, Carmen; Duguet, Nicolas; Rix, Kathryn; Slawin, Alexandra M. Z.; Smith, Andrew D.; Journal of Organic Chemistry; vol. 73; nb. 7; (2008); p. 2784 - 2791 View in Reaxys With thionyl chloride, Time= 8h, Reflux Korkmaz, Neslihan; Astley, Demet; Astley, Stephen T.; Turkish Journal of Chemistry; vol. 35; nb. 3; (2011); p. 361 - 374 View in Reaxys With thionyl chloride, Time= 16h, T= 0 °C , Reflux Welin, Eric R.; Warkentin, Alexander A.; Conrad, Jay C.; MacMillan, David W. C.; Angewandte Chemie - International Edition; vol. 54; nb. 33; (2015); p. 9668 - 9672; Angew. Chem.; vol. 127; nb. 33; (2015); p. 9804 - 9808,5 View in Reaxys
HO
O
O
OH
H N
H
H N
H
NH 2 O
O
Cl
H
O
Rx-ID: 1600840 View in Reaxys 4/10 Yield
Conditions & References
52 %
With thionyl chloride, T= 40 °C Fauchere; Petermann; Helvetica Chimica Acta; vol. 63; nb. 4; (1980); p. 824 - 831 View in Reaxys
H 2N
O
H
NH 2 O
N H
Cl
H
O
Rx-ID: 19162522 View in Reaxys 5/10 Yield
Conditions & References Reaction Steps: 4 1: 80 percent / hydrogen / 10percent Pd/C / acetic acid; methanol / 760 Torr / Ambient temperature 2: 35 percent / MnCl2*4H2O, 1N NaOH, leucine aminopeptidase / H2O / 40 h / 37 °C
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3: 1) 0.5N NaOH / 1) dioxane, 16 h, RT, 2) ether 4: 52 percent / SOCl2 / 40 °C With sodium hydroxide, thionyl chloride, hydrogen, manganese (II) chloride, leucine aminopeptidase, palladium on activated charcoal in methanol, water, acetic acid Fauchere; Petermann; Helvetica Chimica Acta; vol. 63; nb. 4; (1980); p. 824 - 831 View in Reaxys
H
NH 2
O
O
Cl
H
O
Rx-ID: 19162634 View in Reaxys 6/10 Yield
Conditions & References Reaction Steps: 7 1: diethyl ether / -10 °C 2: 75 percent / ethanol 3: 81 percent / H2SO4 4: 80 percent / hydrogen / 10percent Pd/C / acetic acid; methanol / 760 Torr / Ambient temperature 5: 35 percent / MnCl2*4H2O, 1N NaOH, leucine aminopeptidase / H2O / 40 h / 37 °C 6: 1) 0.5N NaOH / 1) dioxane, 16 h, RT, 2) ether 7: 52 percent / SOCl2 / 40 °C With sodium hydroxide, thionyl chloride, sulfuric acid, hydrogen, manganese (II) chloride, leucine aminopeptidase, palladium on activated charcoal in methanol, diethyl ether, ethanol, water, acetic acid Fauchere; Petermann; Helvetica Chimica Acta; vol. 63; nb. 4; (1980); p. 824 - 831 View in Reaxys
H
NH 2
N
O
Cl
H
O
Rx-ID: 19179029 View in Reaxys 7/10 Yield
Conditions & References Reaction Steps: 6 1: 75 percent / ethanol 2: 81 percent / H2SO4 3: 80 percent / hydrogen / 10percent Pd/C / acetic acid; methanol / 760 Torr / Ambient temperature 4: 35 percent / MnCl2*4H2O, 1N NaOH, leucine aminopeptidase / H2O / 40 h / 37 °C 5: 1) 0.5N NaOH / 1) dioxane, 16 h, RT, 2) ether 6: 52 percent / SOCl2 / 40 °C With sodium hydroxide, thionyl chloride, sulfuric acid, hydrogen, manganese (II) chloride, leucine aminopeptidase, palladium on activated charcoal in methanol, ethanol, water, acetic acid Fauchere; Petermann; Helvetica Chimica Acta; vol. 63; nb. 4; (1980); p. 824 - 831 View in Reaxys
N
H
NH 2 O
N H
Cl
H
O
Rx-ID: 19179484 View in Reaxys 8/10 Yield
Conditions & References Reaction Steps: 5 1: 81 percent / H2SO4 2: 80 percent / hydrogen / 10percent Pd/C / acetic acid; methanol / 760 Torr / Ambient temperature 3: 35 percent / MnCl2*4H2O, 1N NaOH, leucine aminopeptidase / H2O / 40 h / 37 °C
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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4: 1) 0.5N NaOH / 1) dioxane, 16 h, RT, 2) ether 5: 52 percent / SOCl2 / 40 °C With sodium hydroxide, thionyl chloride, sulfuric acid, hydrogen, manganese (II) chloride, leucine aminopeptidase, palladium on activated charcoal in methanol, water, acetic acid Fauchere; Petermann; Helvetica Chimica Acta; vol. 63; nb. 4; (1980); p. 824 - 831 View in Reaxys
O H 2N
NH 2 H
Cl
H
NH 2 O
H
Cl
H
O
Rx-ID: 19180602 View in Reaxys 9/10 Yield
Conditions & References Reaction Steps: 3 1: 35 percent / MnCl2*4H2O, 1N NaOH, leucine aminopeptidase / H2O / 40 h / 37 °C 2: 1) 0.5N NaOH / 1) dioxane, 16 h, RT, 2) ether 3: 52 percent / SOCl2 / 40 °C With sodium hydroxide, thionyl chloride, manganese (II) chloride, leucine aminopeptidase in water Fauchere; Petermann; Helvetica Chimica Acta; vol. 63; nb. 4; (1980); p. 824 - 831 View in Reaxys
O H 2N
OH
H
NH 2
H
O
Cl
H
O
Rx-ID: 19150439 View in Reaxys 10/10 Yield
Conditions & References Reaction Steps: 2 1: 1) 0.5N NaOH / 1) dioxane, 16 h, RT, 2) ether 2: 52 percent / SOCl2 / 40 °C With sodium hydroxide, thionyl chloride Fauchere; Petermann; Helvetica Chimica Acta; vol. 63; nb. 4; (1980); p. 824 - 831 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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