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【结 构 式】

【分子编号】25877

【品名】2-[[(2-amino-5-methoxyphenyl)sulfanyl]methyl]-2-ethylhexanoic acid

【CA登记号】

【 分 子 式 】C16H25NO3S

【 分 子 量 】311.44544

【元素组成】C 61.7% H 8.09% N 4.5% O 15.41% S 10.3%

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)

The monosilylation of 2-butyl-2-ethylpropane-1,3-diol (I) with TBDMS-Cl and NaH in THF gives silyl ether (II), which is oxidized with NaIO4 and RuCl3 in CCl4/acetonitrile/water yielding silylated hexanoic acid (III).Elimination of the silyl group of (III) with tetrabutylammonium fluoride (TBAF) affords the hydroxyacid (IV), which is treated with refluxing 48% HBr to give the 2-(bromomethyl)-2-ethylhexanoic acid (V). The condensation of (V) with 2-amino-methoxythiophenol (VI) by means of triethylamine or pyrrolidine in DMF provides intermediate (VII), which is cyclized by means of p-toluenesulfonic acid in refluxing tetradecane to give the 1,5-benzothiazepinone (VIII). The reaction of (VIII) with N-bromosuccinimide (NBS) in dichloromethane yields the 7-bromo derivative (IX), which is treated with bromobenzene (X), K2CO3 and CuBr to afford the 5-phenylbenzothiazepinone (XI). The reduction of the carbonyl group of (XI) with LiAlH4 in ethyl ether gives the benzothiazepine (XII), which is then oxidized with OsO4 in THF/ tert-butanol yielding the S,S-dioxide (XIII). Finally, this compound is demethylated with AlBr3 and ethanethiol in dichloromethane.

1 Brieaddy, L.E.; Handlon, A.L.; Hodgson, G.L. Jr. (Glaxo Wellcome plc); Hypolipidemic benzothiazepines. EP 0792268; JP 1999500102; US 5998400; WO 9616051 .
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) 25871 2-butyl-2-ethyl-1,3-propanediol 115-84-4 C9H20O2 详情 详情
(II) 25872 2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-2-ethyl-1-hexanol C15H34O2Si 详情 详情
(III) 25873 2-([[tert-butyl(dimethyl)silyl]oxy]methyl)-2-ethylhexanoic acid C15H32O3Si 详情 详情
(IV) 25874 2-ethyl-2-(hydroxymethyl)hexanoic acid C9H18O3 详情 详情
(V) 25875 2-(bromomethyl)-2-ethylhexanoic acid C9H17BrO2 详情 详情
(VI) 25876 2-amino-5-methoxyphenylhydrosulfide; 5-Methoxy-2-aminothiophenol;2-Mercapto-4-methoxyaniline;2-amino-5-methoxybenzenethiol;2-Amino-5-methoxy-1-benzenethiol 6274-29-9 C7H9NOS 详情 详情
(VII) 25877 2-[[(2-amino-5-methoxyphenyl)sulfanyl]methyl]-2-ethylhexanoic acid C16H25NO3S 详情 详情
(VIII) 25878 3-butyl-3-ethyl-8-methoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one C16H23NO2S 详情 详情
(IX) 25879 7-bromo-3-butyl-3-ethyl-8-methoxy-2,3-dihydro-1,5-benzothiazepin-4(5H)-one C16H22BrNO2S 详情 详情
(X) 13365 Monobromobenzene; 1-Bromobenzene;Phenylbromide;bromobenzene 108-86-1 C6H5Br 详情 详情
(XI) 25880 7-bromo-3-butyl-3-ethyl-8-methoxy-5-phenyl-2,3-dihydro-1,5-benzothiazepin-4(5H)-one C22H26BrNO2S 详情 详情
(XII) 25881 7-bromo-3-butyl-3-ethyl-5-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepin-8-yl methyl ether; 7-bromo-3-butyl-3-ethyl-8-methoxy-5-phenyl-2,3,4,5-tetrahydro-1,5-benzothiazepine C22H28BrNOS 详情 详情
(XIII) 25882 7-bromo-3-butyl-3-ethyl-8-methoxy-5-phenyl-2,3,4,5-tetrahydro-1H-1lambda(6),5-benzothiazepine-1,1-dione C22H28BrNO3S 详情 详情
Extended Information