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【结 构 式】

【分子编号】31589

【品名】2-oxobutyl 4-methylbenzenesulfonate

【CA登记号】

【 分 子 式 】C11H14O4S

【 分 子 量 】242.29576

【元素组成】C 54.53% H 5.82% O 26.41% S 13.23%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(XXV)

The reaction of 1-hydroxy-2-butanone (XXIV) with tosyl chloride gives the tosylate (XXV), which is condensed with 5-methoxy-1H-benzimidazole-2-thiol (VIII) yielding 5-methoxy-2-(2-oxobutylsulfanyl)-1H-benzimidazole (XXVI). The reaction of (XXVI) with 3-methoxy-2-methyl-2-propenal (XXI) in basic medium affords the 5-oxohexanal derivative (XXVII), which is cyclized by means of NH4OAc and NH3 to give the dihydropyridine (XXVIII). Finally, this compound is dehydrogenated and oxidized to the target sulfinyl derivative.

1 Bekhazi, M.; Zoghbi, M. (PDi-Research Laboratories, Inc. ); Synthesis of omeprazole-type pyridine derivs. and intermediates thereof. WO 9729103 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VIII) 29924 5-Methoxy-1H-benzimidazol-2-ylhydrosulfide; 2-Mercapto-5-methoxybenzimidazole; 5-Methoxy-1H-benzimidazole-2-thiol; 5-Methoxy-2-mercaptbenzimidazole; 5-Methoxy-2-Benzimidazolethiol 37052-78-1 C8H8N2OS 详情 详情
(XXI) 31585 (E)-3-methoxy-2-methyl-2-propenal C5H8O2 详情 详情
(XXIV) 31588 1-hydroxy-2-butanone 5077-67-8 C4H8O2 详情 详情
(XXV) 31589 2-oxobutyl 4-methylbenzenesulfonate C11H14O4S 详情 详情
(XXVI) 31590 1-[(5-methoxy-1H-benzimidazol-2-yl)sulfanyl]-2-butanone C12H14N2O2S 详情 详情
(XXVII) 31591 3-methoxy-6-[(5-methoxy-1H-benzimidazol-2-yl)sulfanyl]-2,4-dimethyl-5-oxohexanal C17H22N2O4S 详情 详情
(XXVIII) 31592 2-[[(5-methoxy-1H-benzimidazol-2-yl)sulfanyl]methyl]-3,5-dimethyl-1,4-dihydro-4-pyridinyl methyl ether; 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-1,4-dihydro-2-pyridinyl)methyl]sulfanyl]-1H-benzimidazole C17H21N3O2S 详情 详情

合成路线2

该中间体在本合成路线中的序号:(XXV)

The reaction of tosylate (XXV) with potassium ethylxanthate (XXIX) gives the adduct (XXX), which is cyclized with 3-methoxy-2-methyl-2-propenal (XXI) by means of t-BuOK, NH4Cl and NH3 in THF yielding the dihydropyridine (XXXI). The oxidation of (XXXI) with MCPBA in chloroform affords the pyridine (XXXII), with simultaneous formation of the sulfinyl group. Finally, this compound is cyclized with 4-methoxyphenylene-1,2-diamine (XXXIII) by means of TFA in refluxing toluene.

1 Bekhazi, M.; Zoghbi, M. (PDi-Research Laboratories, Inc. ); Synthesis of omeprazole-type pyridine derivs. and intermediates thereof. WO 9729103 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXI) 31585 (E)-3-methoxy-2-methyl-2-propenal C5H8O2 详情 详情
(XXV) 31589 2-oxobutyl 4-methylbenzenesulfonate C11H14O4S 详情 详情
(XXIX) 29923 o-Ethylxanthic acid potassium salt; Potassium ethyl xanthogenate; potassium 1-(carbodithioatooxy)ethane 140-89-6 C3H5KOS2 详情 详情
(XXX) 31593 O-ethyl S-(2-oxobutyl) carbonodithioate C7H12O2S2 详情 详情
(XXXI) 31594 S-[(4-methoxy-3,5-dimethyl-1,4-dihydro-2-pyridinyl)methyl] O-methyl carbonodithioate C11H17NO2S2 详情 详情
(XXXII) 31595 O-methyl [(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl](oxo)-lambda(4)-sulfanecarbothioate C11H15NO3S2 详情 详情
(XXXIII) 29922 2-amino-4-methoxyphenylamine; 4-methoxy-1,2-benzenediamine 102-51-2 C7H10N2O 详情 详情
Extended Information