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【结 构 式】

【分子编号】62433

【品名】(1S,2S)-2-bromo-3-ethoxy-1-(4-methoxyphenyl)-3-oxopropyl butyrate

【CA登记号】

【 分 子 式 】C16H21BrO5

【 分 子 量 】373.24374

【元素组成】C 51.49% H 5.67% Br 21.41% O 21.43%

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:(III)

Electrophilic bromination of ethyl p-methoxycinnamate (I) by means of N-bromosuccinimide in moist acetone gave rise to the racemic erythro bromohydrin (II), which was esterified with butyric anhydride to produce the racemic bromoester (III). Kinetic resolution of (III) employing Candida cylindracea lipase caused the enantioselective hydrolysis of the (S,S)-enantiomer, yielding the chiral bromohydrin (V). Cyclization of (V) in the presence of NaOMe furnished epoxide (VI). The target thiazepinone (VIII) was then obtained by condensation between the glycidic ester (VI) and 2-aminobenzenethiol (VII)

1 McCague, R.; Wang, S.; Taylor, S.J.C. (Celltech Group plc); Chiral arylpropionates and their use. WO 9413828 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 25047 butyric anhydride 106-31-0 C8H14O3 详情 详情
(I) 62431 ethyl (E)-3-(4-methoxyphenyl)-2-propenoate C12H14O3 详情 详情
(II) 62432 ethyl (2S,3S)-2-bromo-3-hydroxy-3-(4-methoxyphenyl)propanoate C12H15BrO4 详情 详情
(III) 62433 (1S,2S)-2-bromo-3-ethoxy-1-(4-methoxyphenyl)-3-oxopropyl butyrate C16H21BrO5 详情 详情
(IV) 62434 (1R,2R)-2-bromo-3-ethoxy-1-(4-methoxyphenyl)-3-oxopropyl butyrate C16H21BrO5 详情 详情
(V) 62432 ethyl (2S,3S)-2-bromo-3-hydroxy-3-(4-methoxyphenyl)propanoate C12H15BrO4 详情 详情
(VI) 62435 ethyl (2R,3S)-3-(4-methoxyphenyl)-2-oxiranecarboxylate C12H14O4 详情 详情
(VII) 25182 2-aminobenzenethiol 137-07-5 C6H7NS 详情 详情
(VIII) 62436 (2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one C16H15NO3S 详情 详情
Extended Information