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【结 构 式】

【分子编号】55030

【品名】(2S,3S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-hydroxy-4-{[(4-methylphenyl)sulfonyl]oxy}butyl 4-methylbenzenesulfonate

【CA登记号】

【 分 子 式 】C26H25NO9S2

【 分 子 量 】559.61784

【元素组成】C 55.8% H 4.5% N 2.5% O 25.73% S 11.46%

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:(XX)

Alternatively, the reaction of the cyclic sulfate (VIII) with potassium phthalimide (XVIII) gives the N-substituted phthalimide (XIX), whose sulfate group is cleaved with sulfuric acid to yield the alcohol (XX). The reaction of (XX) with the perhydroisoquinoline (XV) by means of K2CO3 in acetonitrile/methanol affords the oxazoline (XXI), whose ring is opened with thiophenol (XVII) and KHCO3 in THF, providing a mixture of the two sulfides (XXII) and (XXIII) that are not isolated. The cleavage of the phthalimido group with refluxing ethanolamine followed by a treatment with benzoic acid gives a mixture of ammonium salts that is separated by crystallization, yielding the desired isomer (XXIV). The reaction of (XXIV) with acid chloride (XII) affords the precursor (XXV), which is finally deacetylated with NaOH to provide the target compound.

1 Albizati, K.F.; et al.; A synthesis of the HIV-protease inhibitor nelfinavir from D-tartaric acid. Tetrahedron Lett 2001, 42, 37, 6481.
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) 55023 [(4R,5R)-5-({[(4-methylphenyl)sulfonyl]oxy}methyl)-2,2-dioxo-1,3,2lambda~6~-dioxathiolan-4-yl]methyl 4-methylbenzenesulfonate C18H20O10S3 详情 详情
(XII) 46596 3-(chlorocarbonyl)-2-methylphenyl acetate C10H9ClO3 详情 详情
(XV) 13955 (3S,4aS,8aS)-N-(tert-Butyl)decahydro-3-isoquinolinecarboxamide C14H26N2O 详情 详情
(XVII) 12951 Benzenethiol; Phenylmercaptan; Phenylhydrosulfide 108-98-5 C6H6S 详情 详情
(XVIII) 27890 Potassium phthalimide 1074-82-4 C8H4KNO2 详情 详情
(XIX) 55029 potassium 2-[(1S,2S)-3-{[(4-methylphenyl)sulfonyl]oxy}-1-({[(4-methylphenyl)sulfonyl]oxy}methyl)-2-(sulfonatooxy)propyl]-1,3-dioxoisoindoline C26H24KNO12S3 详情 详情
(XX) 55030 (2S,3S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-hydroxy-4-{[(4-methylphenyl)sulfonyl]oxy}butyl 4-methylbenzenesulfonate C26H25NO9S2 详情 详情
(XXI) 55031 methyl 2-((4S)-4-{(1R)-2-[(3S,4aS,8aS)-3-[(tert-butylamino)carbonyl]octahydro-2(1H)-isoquinolinyl]-1-hydroxyethyl}-4,5-dihydro-1,3-oxazol-2-yl)benzoate C27H39N3O5 详情 详情
(XXII) 55032 (3S,4aS,8aS)-N-(tert-butyl)-2-[(2R,3R)-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-hydroxy-4-(phenylsulfanyl)butyl]decahydro-3-isoquinolinecarboxamide C32H41N3O4S 详情 详情
(XXIII) 55033 (3S,4aS,8aS)-N-(tert-butyl)-2-[(2S,3S)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-hydroxy-4-(phenylsulfanyl)butyl]decahydro-3-isoquinolinecarboxamide C32H41N3O4S 详情 详情
(XXIV) 55034 (2R,3R)-4-[(3S,4aS,8aS)-3-[(tert-butylamino)carbonyl]octahydro-2(1H)-isoquinolinyl]-3-hydroxy-1-(phenylsulfanyl)-2-butanaminium benzoate C31H45N3O4S 详情 详情
(XXV) 46497 4-[(3aR,9bR)-9-methoxy-1,3a,4,9b-tetrahydrochromeno[3,4-c]pyrrol-2(3H)-yl]butanenitrile C16H20N2O2 详情 详情
Extended Information