(2S,3S)-3-[(2-aminophenyl)sulfanyl]-2-hydroxy-3-(4-methoxyphenyl)propanamide -Drug Synthesis Database

【结构式】

【分子编号】62464

【品名】(2S,3S)-3-[(2-aminophenyl)sulfanyl]-2-hydroxy-3-(4-methoxyphenyl)propanamide

【CA登记号】

【分子式】C₁₆H₁₈N₂O₃S

【分子量】318.3966

【元素组成】C 60.36% H 5.7% N 8.8% O 15.07% S 10.07%

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：(XLVIII)

In a variation of the preceding methods, the chiral glycidic amide (XLVII) was used as the synthetic precursor. Amide (XLVII) was either prepared by treatment of the chiral glycidic ester (VI) with ammonia, or by enzymatic resolution of (XII), followed by amidation. Iron-catalyzed addition of 2-aminothiophenol (VII) to the glycidamide (XLVII) in refluxing chlorobenzene yielded the desired threo adduct (XLVIII) as the major isomer. Cyclization of amino amide (XLVIII) under acidic conditions furnished thiazepinone (VIII)

参考文献中间体

合成目标

【1】 Yamada, S.; Tsujioka, I.; Shibatini, T.; Yoshioka, R.; Efficient alterative synthetic route to diltiazem via (2R,3S)-3-(4-methoxyphenyl)glycidamide. Chem Pharm Bull 1999, 47, 2, 146.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(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
(XII)	11905	methyl (2R,3S)-3-(4-methoxyphenyl)-2-oxiranecarboxylate		C₁₁H₁₂O₄	详情	详情
(XLVII)	62463	(2R,3S)-3-(4-methoxyphenyl)-2-oxiranecarboxamide		C₁₀H₁₁NO₃	详情	详情
(XLVIII)	62464	(2S,3S)-3-[(2-aminophenyl)sulfanyl]-2-hydroxy-3-(4-methoxyphenyl)propanamide		C₁₆H₁₈N₂O₃S	详情	详情

Extended Information