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【结 构 式】 
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【分子编号】17197 【品名】(2R)-2-[(2S,3R)-3-isopropyl-4-oxoazetidinyl]propionic acid 【CA登记号】 |
【 分 子 式 】C9H15NO3 【 分 子 量 】185.22304 【元素组成】C 58.36% H 8.16% N 7.56% O 25.91% |
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：(X)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.
| 【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