(3R,6R,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid ethyl ester

Base Information

Chemical Name:(3R,6R,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid ethyl ester
CAS No.:214151-23-2
Molecular Formula:C₁₇H₂₂N₂O₅S₂
Molecular Weight:398.504
Hs Code.:

Synonyms:(3R,6R,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid ethyl ester

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Chemical Property of (3R,6R,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid ethyl ester

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Technology Process of (3R,6R,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid ethyl ester

There total 7 articles about (3R,6R,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 72.0%

: 214151-21-0
(3R,6R,8aS)-6-Amino-5-oxo-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid ethyl ester

: 1939-99-7
benzenesulfonyl chloride

: 214151-23-2
(3R,6R,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid ethyl ester

Guidance literature:: With triethylamine; In dichloromethane; Ambient temperature;
DOI:10.1021/jm981013e

Reference yield:

: 27025-22-5
D-glutamic acid-5-methyl ester; hydrochloride

: 214151-23-2
(3R,6R,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: Et₃N / dimethylformamide / 16 h

2: 73 percent / DMAP, DCC / CH₂Cl₂ / 15 h / Ambient temperature

3: 48 percent / DIBAL-H / toluene; diethyl ether; CH₂Cl₂ / -78 - -50 °C

4: NaOAc, AcOH, H₂O / ethanol / 17 h / Ambient temperature

5: benzyltrimethylammonium fluoride / dimethylformamide / 4 h / Ambient temperature

6: 1 M aq.HCl / CH₂Cl₂ / 4 h

7: 61 percent / NH₂NH₂*H₂O / CHCl₃; ethanol / 48 h / Ambient temperature

8: 72 percent / Et₃N / CH₂Cl₂ / Ambient temperature

With hydrogenchloride; dmap; water; sodium acetate; trimethyl(benzyl)ammonium fluoride; diisobutylaluminium hydride; hydrazine hydrate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; In diethyl ether; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm981013e

Reference yield:

: (R)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-pentanedioic acid 5-methyl ester

: 214151-23-2
(3R,6R,8aS)-5-Oxo-6-phenylmethanesulfonylamino-hexahydro-thiazolo[3,2-a]pyridine-3-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 73 percent / DMAP, DCC / CH₂Cl₂ / 15 h / Ambient temperature

2: 48 percent / DIBAL-H / toluene; diethyl ether; CH₂Cl₂ / -78 - -50 °C

3: NaOAc, AcOH, H₂O / ethanol / 17 h / Ambient temperature

4: benzyltrimethylammonium fluoride / dimethylformamide / 4 h / Ambient temperature

5: 1 M aq.HCl / CH₂Cl₂ / 4 h

6: 61 percent / NH₂NH₂*H₂O / CHCl₃; ethanol / 48 h / Ambient temperature

7: 72 percent / Et₃N / CH₂Cl₂ / Ambient temperature

With hydrogenchloride; dmap; water; sodium acetate; trimethyl(benzyl)ammonium fluoride; diisobutylaluminium hydride; hydrazine hydrate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; In diethyl ether; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm981013e