S-[(3R)-5-oxopyrrolidinyl] (2R)-2-[(2S,3R)-3-isopropyl-4-oxoazetidinyl]propanethioate -Drug Synthesis Database

【结构式】

【分子编号】17198

【品名】S-[(3R)-5-oxopyrrolidinyl] (2R)-2-[(2S,3R)-3-isopropyl-4-oxoazetidinyl]propanethioate

【CA登记号】

【分子式】C₁₃H₂₀N₂O₃S

【分子量】284.37948

【元素组成】C 54.91% H 7.09% N 9.85% O 16.88% S 11.28%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XI)

2) The esterification of 2(R)-[4-oxo-3(S)-[1(R)-(trimethylsilyloxy)ethyl]azetidin-2(S)-yl]propionic acid (X) with the previously obtained pyrrolidinone (V) gives the expected thiopropionic ester (XI), which is acylated with oxalic acid monochloride monopivaloyloxymethyl ester (XII) by means of trimethylsilylchloride and triethylamine yielding the condensation product (XIII). The cyclization of (XIII) by means of methylphosphonic acid diethyl ester affords silylated CS-834 (XIV), which is finally deprotected with 1N HCl.

参考文献中间体

合成目标

【1】 Graul, A.; Castañer, R.M.; Castañer, J.; Leeson, P.; CS-834. Drugs Fut 1998, 23, 3, 261.
【2】 Yasuda, H.; Kuwahara, S.; Kawamoto, I.; Miyauchi, M.; Endo, R.; Hisaoka, M.; CS-834, a new oral carbapenem: I. Structure-activity relationships of 2-substituted 1beta-methylcarbapenems. 36th Intersci Conf Antimicrob Agents Chemother (Sept 15-18, New Orleans) 1996, Abst F105.
【3】 Oita, S.; Mori, M. (Sankyo Co., Ltd.); Carbapenem ester preparation. JP 1996059663 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	17192	(4R)-4-sulfanyltetrahydro-2H-pyrrol-2-one	157429-42-0	C₄H₇NOS	详情	详情
(X)	17197	(2R)-2-[(2S,3R)-3-isopropyl-4-oxoazetidinyl]propionic acid		C₉H₁₅NO₃	详情	详情
(XI)	17198	S-[(3R)-5-oxopyrrolidinyl] (2R)-2-[(2S,3R)-3-isopropyl-4-oxoazetidinyl]propanethioate		C₁₃H₂₀N₂O₃S	详情	详情
(XII)	17199	[(2-chloro-2-oxoacetyl)oxy]methyl pivalate		C₈H₁₁ClO₅	详情	详情
(XIII)	17200	([2-[(2S,3R)-3-isopropyl-2-((1R)-1-methyl-2-oxo-2-[[(3R)-5-oxopyrrolidinyl]sulfanyl]ethyl)-4-oxoazetidinyl]-2-oxoacetyl]oxy)methyl pivalate		C₂₁H₃₀N₂O₈S	详情	详情
(XIV)	17201	[(2,2-dimethylpropanoyl)oxy]methyl (4R,5S,6R)-6-isopropyl-4-methyl-7-oxo-3-[[(3R)-5-oxopyrrolidinyl]sulfanyl]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate		C₂₁H₃₀N₂O₆S	详情	详情

Extended Information