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【结 构 式】

【分子编号】61454

【品名】1-allyl 3-ethyl 4-hydroxy-1,3-pyrrolidinedicarboxylate

【CA登记号】

【 分 子 式 】C11H17NO5

【 分 子 量 】243.25972

【元素组成】C 54.31% H 7.04% N 5.76% O 32.89%

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:(VI)

Michael addition of ethyl acrylate (I) to glycine ethyl ester (II) produces the amino diester (III), which is protected as the allyl carbamate (IV) by treatment with allyl chloroformate. Dieckmann cyclization of diester (IV) in the presence of NaH leads to pyrrolidinone (V). After reduction of (V) to the corresponding alcohol (VI) with NaBH4, dehydration by means of methanesulfonyl chloride and pyridine furnishes the conjugated ester (VII). Acid (VIII), obtained by alkaline hydrolysis of (VII), is then condensed with magnesium tert-butyl malonate in the presence of CDI to produce keto ester (IX). Chlorination of (IX) with sulfuryl chloride, followed by acidic decarboxylation gives rise to chloro ketone (X). This is then condensed with ammonium dithiocarbamate to generate the 2-mercapto thiazole (XI)

1 Sunagawa, M.; Itoh, M.; Kubota, K.; et al.; New anti-MRSA and anti-VRE carbapenems; synthesis and structure-activity relationships of 1beta-methyl-2-(thiazol-2-ylthio)carbapenems. J. Antibiot. 2002, 55, 8, 722.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10164 ethyl acrylate 140-88-5 C5H8O2 详情 详情
(II) 10309 ethyl 2-aminoacetate; Glycine ethyl ester 459-73-4 C4H9NO2 详情 详情
(III) 61451 ethyl 3-[(2-ethoxy-2-oxoethyl)amino]propanoate C9H17NO4 详情 详情
(IV) 61452 ethyl 3-[[(allyloxy)carbonyl](2-ethoxy-2-oxoethyl)amino]propanoate C13H21NO6 详情 详情
(V) 61453 1-allyl 3-ethyl 4-oxo-1,3-pyrrolidinedicarboxylate C11H15NO5 详情 详情
(VI) 61454 1-allyl 3-ethyl 4-hydroxy-1,3-pyrrolidinedicarboxylate C11H17NO5 详情 详情
(VII) 61455 1-allyl 3-ethyl 2,5-dihydro-1H-pyrrole-1,3-dicarboxylate C11H15NO4 详情 详情
(VIII) 61456 1-[(allyloxy)carbonyl]-2,5-dihydro-1H-pyrrole-3-carboxylic acid C9H11NO4 详情 详情
(IX) 61457 allyl 3-[3-(tert-butoxy)-3-oxopropanoyl]-2,5-dihydro-1H-pyrrole-1-carboxylate C15H21NO5 详情 详情
(X) 61458 allyl 3-(2-chloroacetyl)-2,5-dihydro-1H-pyrrole-1-carboxylate C10H12ClNO3 详情 详情
(XI) 61459 allyl 3-(2-sulfanyl-1,3-thiazol-4-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate C11H12N2O2S2 详情 详情
Extended Information