【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% |
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 |