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【结 构 式】

【分子编号】27584

【品名】[(4S,5S)-2-[(2S)-2-(1,3-benzodioxol-5-yl)-2-(2-bromo-6-butyl-3-pyridinyl)ethyl]-5-[4-(methylsulfanyl)phenyl]-4,5-dihydro-1,3-oxazol-4-yl]methyl methyl ether

【CA登记号】

【 分 子 式 】C30H33BrN2O4S

【 分 子 量 】597.5731

【元素组成】C 60.3% H 5.57% Br 13.37% N 4.69% O 10.71% S 5.37%

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:(XXXIX)

In a related procedure, chiral oxazoline (XXXV) was prepared by condensation of ethyl acetimidate (XXXIII) with (S,S)-thiomicamine (XXXII), followed by O-methylation with MeI and sodium tert-pentoxide. Condensation of the lithium salt of (XXXV) with diethylchlorophosphate at -78 C provided phosphonate (XXXVI), which was submitted to a Horner-Emmons reaction with pyridine aldehyde (XV) to yield the vinyl oxazoline (XXXVII). Conjugate addition of the organolithium reagent (XXXVIII) to (XXXVII) then produced adduct (XXXIX) as the major diastereoisomer. Hydrolysis of the oxazoline of (XXXIX) upon refluxing in isopropyl alcohol with H2SO4 yielded isopropyl ester (XL). Pyridine carboxylate (XLI) was further obtained by carbonylation of (XL) under atmosphere of CO in the presence of bis(diphenylphosphino)ferrocene and palladium diacetate in MeOH.

1 Frey, L.F.; Devine, P.N.; Tschaen, D.M.; Dolling, U.H.; Tillyer, R.D.; Kato, Y. (Banyu Pharmaceutical Co., Ltd.; Merck & Co., Inc.); Stereoselective deoxygenation reaction. EP 0923557; JP 1999514676; WO 9806700 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XV) 27563 2-bromo-6-butylnicotinaldehyde C10H12BrNO 详情 详情
(XXXII) 27578 (1S,2S)-2-amino-1-[4-(methylsulfanyl)phenyl]-1,3-propanediol C10H15NO2S 详情 详情
(XXXIII) 12831 ethyl ethanimidoate 1000-84-6 C4H9NO 详情 详情
(XXXIV) 27579 [(4S,5S)-2-methyl-5-[4-(methylsulfanyl)phenyl]-4,5-dihydro-1,3-oxazol-4-yl]methanol C12H15NO2S 详情 详情
(XXXV) 27580 (4S,5S)-4-(methoxymethyl)-2-methyl-5-[4-(methylsulfanyl)phenyl]-4,5-dihydro-1,3-oxazole C13H17NO2S 详情 详情
(XXXVI) 27581 diethyl [(4S,5S)-4-(methoxymethyl)-5-[4-(methylsulfanyl)phenyl]-4,5-dihydro-1,3-oxazol-2-yl]methylphosphonate C17H26NO5PS 详情 详情
(XXXVII) 27582 2-bromo-6-butyl-3-((E)-2-[(4S,5S)-4-(methoxymethyl)-5-[4-(methylsulfanyl)phenyl]-4,5-dihydro-1,3-oxazol-2-yl]ethenyl)pyridine C23H27BrN2O2S 详情 详情
(XXXVIII) 27583 1,3-benzodioxol-5-yllithium C7H5LiO2 详情 详情
(XXXIX) 27584 [(4S,5S)-2-[(2S)-2-(1,3-benzodioxol-5-yl)-2-(2-bromo-6-butyl-3-pyridinyl)ethyl]-5-[4-(methylsulfanyl)phenyl]-4,5-dihydro-1,3-oxazol-4-yl]methyl methyl ether C30H33BrN2O4S 详情 详情
(XL) 27585 isopropyl (3S)-3-(1,3-benzodioxol-5-yl)-3-(2-bromo-6-butyl-3-pyridinyl)propanoate C22H26BrNO4 详情 详情
(XLI) 27586 methyl 3-[(1S)-1-(1,3-benzodioxol-5-yl)-3-isopropoxy-3-oxopropyl]-6-butyl-2-pyridinecarboxylate C24H29NO6 详情 详情
Extended Information