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【结 构 式】

【分子编号】60419

【品名】7-methoxy-3,4-dihydro-1,4-benzothiazepin-5(2H)-one

【CA登记号】

【 分 子 式 】C10H11NO2S

【 分 子 量 】209.26888

【元素组成】C 57.4% H 5.3% N 6.69% O 15.29% S 15.32%

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:(VII)

Treatment of 2,5-dihydroxybenzoic acid (I) with dimethyl sulfate and K2CO3 afforded methyl 2-hydroxy-5-methoxybenzoate (II). Condensation of (II) with dimethylthiocarbamoyl chloride gave the O-aryl thiocarbamate (III), which underwent thermal rearrangement to the S-aryl isomer (IV) upon heating at 265 C in diphenyl ether. Subsequent hydrolysis of the thiocarbamate group of (IV) furnished the desired thiophenol compound (V). Cyclization of the mercapto ester (V) with 2-chloroethylamine (VI) gave rise to the benzothiazepinone (VII), which was further reduced to the benzothiazepine (VIII) using LiAlH4. Acylation of (VIII) with acryloyl chloride (IX) provided the acrylamide (X). Finally, Michael addition of 4-benzylpiperidine (XI) to acrylamide (X) yielded the title compound.

1 Kaneko, N.; Oosawa, T.; Sakai, T.; Oota, H. (Kirin Brewery Co., Ltd.); 1,4-Benzothiazepine derivs.. EP 0565721; US 5416066; WO 9212148 .
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) 60415 2,5-dihydroxybenzoic acid C7H6O4 详情 详情
(II) 60416 methyl 2-hydroxy-5-methoxybenzoate C9H10O4 详情 详情
(III) 60417 methyl 2-{[(dimethylamino)carbothioyl]oxy}-5-methoxybenzoate C12H15NO4S 详情 详情
(IV) 60418 methyl 2-{[(dimethylamino)carbonyl]sulfanyl}-5-methoxybenzoate C12H15NO4S 详情 详情
(V) 13887 methyl 5-methoxy-2-sulfanylbenzoate C9H10O3S 详情 详情
(VI) 33455 2-chloro-1-ethanamine; 2-chloroethylamine C2H6ClN 详情 详情
(VII) 60419 7-methoxy-3,4-dihydro-1,4-benzothiazepin-5(2H)-one C10H11NO2S 详情 详情
(VIII) 60420 7-methoxy-2,3,4,5-tetrahydro-1,4-benzothiazepine; methyl 2,3,4,5-tetrahydro-1,4-benzothiazepin-7-yl ether C10H13NOS 详情 详情
(IX) 11577 Acryloyl chloride; Acrylyl chloride;2-Propenoyl chloride 814-68-6 C3H3ClO 详情 详情
(X) 60421 1-[7-methoxy-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl]-2-propen-1-one C13H15NO2S 详情 详情
(XI) 26225 4-benzylpiperidine 31252-42-3 C12H17N 详情 详情
Extended Information