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Date
25 reactions in Reaxys
2018-03-20 14h:30m:50s (EST)
O
1. Query HO H 2N
Search as: As drawn AND (IDE.XRN=2803960)
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O N
HO
H 2N
H 2N
Rx-ID: 25967228 View in Reaxys 1/25 Yield
Conditions & References With hydrogenchloride, Time= 3h, Heating Wang, Boyuan; Zhang, Wei; Zhang, Leilei; Du, Da-Ming; Liu, Gang; Xu, Jiaxi; European Journal of Organic Chemistry; nb. 2; (2008); p. 350 - 355 View in Reaxys With hydrogenchloride, water Drabina, Pavel; Karel, Sergej; Panov, Illia; Sedlak, Milos; Tetrahedron Asymmetry; vol. 24; nb. 5-6; (2013); p. 334 - 339 View in Reaxys
O
O HO
H 2N
Rx-ID: 35129151 View in Reaxys 2/25 Yield
Conditions & References Reaction Steps: 2 1: ammonia 2: hydrogenchloride; water With hydrogenchloride, ammonia, water, 1: |Strecker Aminoacid Synthesis Drabina, Pavel; Karel, Sergej; Panov, Illia; Sedlak, Milos; Tetrahedron Asymmetry; vol. 24; nb. 5-6; (2013); p. 334 - 339 View in Reaxys
O HO
H 2N
Rx-ID: 7789530 View in Reaxys 3/25 Yield
Conditions & References Weinges,K. et al.; Chemische Berichte; vol. 104; (1971); p. 3594 - 3606 View in Reaxys Cohen; Lo; Journal of Biological Chemistry; vol. 245; (1970); p. 5718,5724 View in Reaxys Patent; BASF AG; FR2237892; (1975); DE2336718; ; vol. 82; nb. 156263 View in Reaxys Developed one-minute LC-MS methods for the following substrate/product pairs: Cinnamic acid and phenylalanine; 2-bromocinnamic acid and 2-bromophenylalanine; α-methyl cinnamic acid and α-methylphenylalanine Patent; VERENIUM CORPORATION; US2011/27346; (2011); (A1) English View in Reaxys Developed one-minute LC-MS methods for the following substrate/product pairs: Cinnamic acid and phenylalanine; 2-bromocinnamic acid and 2-bromophenylalanine; α-methyl cinnamic acid and α-methylphenylalanine. Patent; Weiner, David P.; Varvak, Alexander; Richardson, Toby; Podar, Mircea; Burke, Ellen; Healey, Shaun; US2012/177722; (2012); (A1) English View in Reaxys
Copyright © 2018 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
Br
N
O
E
O
HO
H 2N
Rx-ID: 9254362 View in Reaxys 4/25 Yield
Conditions & References With sodium hydroxide, N,N'-ethylenebis(salicylideneiminato)copper(II) in toluene, Time= 48h, T= 20 °C Belokon', Yuri N.; Bhave, Devayani; D'Addario, Daniela; Groaz, Elizabetta; Maleev, Viktor; North, Michael; Pertrosyan, Armine; Tetrahedron Letters; vol. 44; nb. 10; (2003); p. 2045 - 2048 View in Reaxys
OH O
Br
N
O
E
HO
O
H 2N
Rx-ID: 9138071 View in Reaxys 5/25 Yield 98 % Chromat.
Conditions & References Stage 1: With (R,R)-dicyclohexyl tartrate, lithium diisopropyl amide in tetrahydrofuran, Time= 0.5h, T= -60 °C Stage 2: in tetrahydrofuran, Time= 12h, T= 25 °C Stage 3: With hydrogenchloride in tetrahydrofuran, water, Time= 10h, Heating Hu, Ai-Guo; Zhang, Ling-Yun; Wang, Shan-Wei; Wang, Ji-Tao; Synthetic Communications; vol. 32; nb. 14; (2002); p. 2143 - 2147 View in Reaxys
O
O
N O
Br
HO
H 2N
Rx-ID: 8688447 View in Reaxys 6/25 Yield 83 %
Conditions & References Stage 1: With sodium hydroxide, tetraethylammonium bromide, (R,R)-TADDOL in toluene, Time= 12h, T= 15 - 20 °C , Substitution Stage 2: With hydrogenchloride in water, Time= 0.25h, Hydrolysis, Further stages. Belokon, Yuri N.; Kochetkov, Konstantin A.; Churkina, Tatiana D.; Ikonnikov, Nikolai S.; Chesnokov, Alexey A.; Larionov, Oleg V.; Singh, Ishwar; Parmar, Virinder S.; Vyskocil, Stepan; Kagan, Henri B.; Journal of Organic Chemistry; vol. 65; nb. 21; (2000); p. 7041 - 7048 View in Reaxys
O
Br
N
O
E
O
HO
H 2N
Rx-ID: 8520464 View in Reaxys 7/25 Yield 94 %
Conditions & References Stage 1: With cesium hydroxide, (R,R)-TADDOL in toluene, Time= 12h, T= 15 - 20 °C , Alkylation, benzylation Stage 2: With hydrogenchloride in water, toluene, Heating, Hydrolysis Belokon'; Kochetkov; Churkina; Ikonnikov; Chesnokov; Larionov; Kagan; Russian Chemical Bulletin; vol. 48; nb. 5; (1999); p. 917 - 923 View in Reaxys
Copyright © 2018 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
O O
HO
H 2N
O
H 2N
O
H 2N
O O
H 2N
Rx-ID: 4078624 View in Reaxys 8/25 Yield
Conditions & References With phosphate buffer, Humicola amino esterase, Ambient temperature, Title compound not separated from byproducts Liu, Weiguo; Ray, Paul; Benezra, Steven A.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 5; (1995); p. 553 - 560 View in Reaxys
O
O
O NH
HO
H 2N
OH
O
Rx-ID: 4271565 View in Reaxys 9/25 Yield
Conditions & References
89 %
With hydrogenchloride in tetrahydrofuran, Time= 2h, Ambient temperature Zanardi, Franca; Battistini, Lucia; Rassu, Gloria; Cornia, Mara; Casiraghi, Giovanni; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 19; (1995); p. 2471 - 2476 View in Reaxys With ammonium hydroxide, silica gel, trifluoroacetic acid, 1.) MeOH, Yield given. Multistep reaction Casiraghi; Rassu; Synthesis; nb. 6; (1995); p. 607 - 626 View in Reaxys
C O
Br
O HO
H 2N
Rx-ID: 17930099 View in Reaxys 10/25 Yield
Conditions & References Reaction Steps: 6 1: 70 percent / CF3CO2Ag / CH2Cl2 / 2 h / 0 °C 2: 96 percent / 2,6-dimethylpyridine / CH2Cl2 / 1 h / Ambient temperature 3: 66 percent / CF3CO2H / CH2Cl2 / 2 h / 0 °C 4: KMnO4, dicyclohexano-18-crown-6 ether / CH2Cl2 / 2 h / Ambient temperature 6: 89 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature With 2,6-dimethylpyridine, hydrogenchloride, perhydrodibenzo-18-crown-6, potassium permanganate, silver trifluoroacetate, trifluoroacetic acid in tetrahydrofuran, dichloromethane Zanardi, Franca; Battistini, Lucia; Rassu, Gloria; Cornia, Mara; Casiraghi, Giovanni; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 19; (1995); p. 2471 - 2476 View in Reaxys
O
O N
O
HO
H 2N
O
Rx-ID: 17941896 View in Reaxys 11/25 Yield
Conditions & References Reaction Steps: 5 1: 96 percent / 2,6-dimethylpyridine / CH2Cl2 / 1 h / Ambient temperature
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2: 66 percent / CF3CO2H / CH2Cl2 / 2 h / 0 °C 3: KMnO4, dicyclohexano-18-crown-6 ether / CH2Cl2 / 2 h / Ambient temperature 5: 89 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature With 2,6-dimethylpyridine, hydrogenchloride, perhydrodibenzo-18-crown-6, potassium permanganate, trifluoroacetic acid in tetrahydrofuran, dichloromethane Zanardi, Franca; Battistini, Lucia; Rassu, Gloria; Cornia, Mara; Casiraghi, Giovanni; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 19; (1995); p. 2471 - 2476 View in Reaxys
O
O O
N
HO O
H 2N
Rx-ID: 17941917 View in Reaxys 12/25 Yield
Conditions & References Reaction Steps: 3 1: KMnO4, dicyclohexano-18-crown-6 ether / CH2Cl2 / 2 h / Ambient temperature 3: 89 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature With hydrogenchloride, perhydrodibenzo-18-crown-6, potassium permanganate in tetrahydrofuran, dichloromethane Zanardi, Franca; Battistini, Lucia; Rassu, Gloria; Cornia, Mara; Casiraghi, Giovanni; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 19; (1995); p. 2471 - 2476 View in Reaxys
O
O
O N O
HO
HO
H 2N
OH
Rx-ID: 17941967 View in Reaxys 13/25 Yield
Conditions & References Reaction Steps: 2 2: 89 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature With hydrogenchloride in tetrahydrofuran Zanardi, Franca; Battistini, Lucia; Rassu, Gloria; Cornia, Mara; Casiraghi, Giovanni; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 19; (1995); p. 2471 - 2476 View in Reaxys
O
O N
O
HO O
H 2N
Si
Rx-ID: 17941977 View in Reaxys 14/25 Yield
Conditions & References Reaction Steps: 4 1: 66 percent / CF3CO2H / CH2Cl2 / 2 h / 0 °C 2: KMnO4, dicyclohexano-18-crown-6 ether / CH2Cl2 / 2 h / Ambient temperature 4: 89 percent / aq. HCl / tetrahydrofuran / 2 h / Ambient temperature With hydrogenchloride, perhydrodibenzo-18-crown-6, potassium permanganate, trifluoroacetic acid in tetrahydrofuran, dichloromethane
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Zanardi, Franca; Battistini, Lucia; Rassu, Gloria; Cornia, Mara; Casiraghi, Giovanni; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 19; (1995); p. 2471 - 2476 View in Reaxys
O
N
HO
O
H 2N
O
Rx-ID: 4161426 View in Reaxys 15/25 Yield
Conditions & References With hydrogenchloride, acetic acid, Time= 5.5h, T= 95 °C , Heating, Yield given Slavinskaya, V. A.; Sile, D. E.; Katkevich, M. Yu.; Korchagova, E. Kh.; Lukevits, E.; Chemistry of Heterocyclic Compounds (New York, NY, United States); vol. 30; nb. 6; (1994); p. 724 - 728; Khimiya Geterotsiklicheskikh Soedinenii; nb. 6; (1994); p. 829 - 833 View in Reaxys O–
O
N E
O
Ni 2+ –N
Br N
HO
H 2N
O
Rx-ID: 2397476 View in Reaxys 16/25 Yield 95 %
Conditions & References With potassium hydroxide, C-9 in dichloromethane, T= 20 °C Belokon', Yu. N.; Maleev, V. I.; Videnskaya, S. O.; Saporovskaya, M. B.; Tsyryapkin, V. A.; Belikov, V. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 40; nb. 1.1; (1991); p. 110 - 118; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 1; (1991); p. 126 - 134 View in Reaxys
H 2N
O Br
O
HO
N O
O OH
H 2N
Rx-ID: 2396624 View in Reaxys 17/25 Yield 23 %, 63 %
Conditions & References With tetrabutylammomium bromide, potassium carbonate in acetonitrile, Time= 48h, Heating, further alkylation method, Product distribution O'Donnell, Martin J.; Bennett, William D.; Bruder, Willian A.; Jacobsen, William N.; Knuth, Keith; et al.; Journal of the American Chemical Society; vol. 110; nb. 25; (1988); p. 8520 - 8525 View in Reaxys
O Br
O
H 2N
O
N Cl
HO
O OH
H 2N
Rx-ID: 2397011 View in Reaxys 18/25 Yield 94 %, 7 %
Conditions & References With tetrabutylammomium bromide, potassium carbonate in acetonitrile, Time= 48h, Heating, further alkylation method, Product distribution
Copyright © 2018 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'Donnell, Martin J.; Bennett, William D.; Bruder, Willian A.; Jacobsen, William N.; Knuth, Keith; et al.; Journal of the American Chemical Society; vol. 110; nb. 25; (1988); p. 8520 - 8525 View in Reaxys
O
O
O N
HO
H 2N
Rx-ID: 3047382 View in Reaxys 19/25 Yield
Conditions & References With hydrogenchloride, 1.) ether, 12 h, room temp.; 2.) reflux, 4 h, Yield given. Multistep reaction Yaozhong, Jiang; Changyou, Zhou; Shengde, Wu; Daimo, Chen; Youan, Ma; Guilan, Liu; Tetrahedron; vol. 44; nb. 17; (1988); p. 5343 - 5354 View in Reaxys
O Cl
HO
H 2N
Rx-ID: 20797003 View in Reaxys 20/25 Yield
Conditions & References Reaction Steps: 2 1: 96 percent / K2CO3, KOH / benzyl triethylammonium chloride / CH2Cl2 / 6 h / Ambient temperature 2: 1.) hydrochloric acid (1N); 2.) hydrochloric acid (6N) / 1.) ether, 12 h, room temp.; 2.) reflux, 4 h With hydrogenchloride, potassium hydroxide, potassium carbonate, N-benzyl-N,N,N-triethylammonium chloride in dichloromethane Yaozhong, Jiang; Changyou, Zhou; Shengde, Wu; Daimo, Chen; Youan, Ma; Guilan, Liu; Tetrahedron; vol. 44; nb. 17; (1988); p. 5343 - 5354 View in Reaxys
O
N
I HO
O
H 2N
O
Rx-ID: 1089173 View in Reaxys 21/25 Yield
Conditions & References (i) iPr2NEt, (ii) aq. HCl, AcOH, Multistep reaction Kuebel,B. et al.; Chemische Berichte; vol. 112; (1979); p. 128 - 137 View in Reaxys
H N
O
O HO
HN O
H 2N
Rx-ID: 4119666 View in Reaxys 22/25 Yield
Conditions & References With sodium hydroxide, Heating Jean; Anatol; Bulletin de la Societe chimique de France; vol. 10; (1970); p. 3698 - 3703 View in Reaxys
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N N
O
(+-)-2-chloro-2-methyl-3-phenyl-propionic acid
N
HO
N
H 2N
Rx-ID: 7789532 View in Reaxys 23/25 Yield
Conditions & References With 1,4-dioxane Jurkewitsch et al.; Zhurnal Obshchei Khimii; vol. 28; (1958); p. 227,228; engl. Ausg. S. 226, 227 View in Reaxys
O N
O
(+-)-2-amino-2-methyl-3-phenyl-propionitrile hydrochloride
K
HO
H 2N
Rx-ID: 7789533 View in Reaxys 24/25 Yield
Conditions & References With water, ammonium chloride, T= 55 - 60 °C , Behandeln der in Aether loeslichen Anteile des Reaktionsprodukts mit HCl Stein et al.; Journal of the American Chemical Society; vol. 77; (1955); p. 700,702 View in Reaxys
O
(+-)-4-methyl-4-benzyl-imidazolidinedione-(2.5) HO
H 2N
Rx-ID: 7789531 View in Reaxys 25/25 Yield
Conditions & References With barium dihydroxide, water Herbst; Johnson; Journal of the American Chemical Society; vol. 54; (1932); p. 2463,2467 View in Reaxys
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