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【结 构 式】

【分子编号】37486

【品名】(2R,3S)-3-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

【CA登记号】

【 分 子 式 】C19H21NO2S2

【 分 子 量 】359.51328

【元素组成】C 63.48% H 5.89% N 3.9% O 8.9% S 17.84%

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)

The reaction of 2-aminothiophenol (I) with diethyl benzylidenemalonate (II) by heating at 90 C gives diethyl 2-(2-aminophenylthio)-2-phenylethane-1,1-dicarboxylate (III), which is cyclized by heating at 180 C with triethylamine hydrochloride yielding 2,3-dihydro-3-ethoxycarbonyl-2-phenyl-1,5-benzothiazepin-4(5H)-one (IV). The reduction of (IV) with LiAlH4 in THF affords 2,3-dihydro-3-hydroxymethyl-2-phenyl-1,5-benzothiazepin-4(5H)-one (V), which by reaction with SOCl2 in refluxing benzene is converted into 2,3-dihydro-3-chloromethyl-2-phenyl-1,5-benzothiazepin-4(5H)-one (VII). Finally, this compound is treated with N-methylpiperazine at reflux temperature, and acidified with HCl. An alternative way is the reaction of (V) with methanesulfonyl chloride in pyridine affording 2,3-dihydro-3-methanesulfonyloxymethyl-2-phenyl-1,5-benzothiazepin-4(5H)-one (VI), which is then treated with N-methylpiperazine and HCl as before.

1 Izumi, K.; et al.; FR 2416890 .
2 Hillier, K.; Castaner, J.; BTM-1042. Drugs Fut 1981, 6, 9, 534.
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) 10061 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine 109-01-3 C5H12N2 详情 详情
(I) 25182 2-aminobenzenethiol 137-07-5 C6H7NS 详情 详情
(II) 37482 diethyl 2-benzylidenemalonate 5292-53-5 C14H16O4 详情 详情
(III) 37483 diethyl 2-[[(2-aminophenyl)sulfanyl](phenyl)methyl]malonate C20H23NO4S 详情 详情
(IV) 37484 ethyl (2R,3R)-4-oxo-2-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine-3-carboxylate C18H17NO3S 详情 详情
(V) 37485 (2R,3S)-3-(hydroxymethyl)-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one C16H15NO2S 详情 详情
(VI) 37486 (2R,3S)-3-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one C19H21NO2S2 详情 详情
(VII) 37487 (2R,3S)-3-(chloromethyl)-2-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one C16H14ClNOS 详情 详情
Extended Information