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【结 构 式】

【分子编号】60479

【品名】(1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(phenylsulfinyl)-1-ethanamine; (1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(phenylsulfinyl)ethylamine

【CA登记号】

【 分 子 式 】C13H19NO3S

【 分 子 量 】269.3648

【元素组成】C 57.97% H 7.11% N 5.2% O 17.82% S 11.9%

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:(III)

The reaction of the unsaturated acetonide (I) with ammonia gives a diastereomeric, not separable mixture, of amino derivatives (II) + (III), which is reduced with BF3/Et2O and NaI to yield a mixture of sulfanyl derivatives (IV)+ (V). The condensation of this mixture with 3-acetoxy-2-methylbenzoic acid (VI) by means of EDC and HOBT affords a separable mixture of amides, from which the desired diastereomer (VII) is isolated. The hydrolysis of the acetonide group of (VII) by means of HCl in methanol provide the dihydroxyamide (VIII), which is finally condensed with the perhydroisoquinoline (IX) by means of Tes-Cl and TEA to furnish the target Nelfinavir.

1 Ma, D.; et al.; A short synthesis of the HIV-protease inhibitor nelfinavir via a diastereoselective addition of ammonia to the alpha,beta-unsaturated sulfoxide derived from (R)-glyceraldehyde acetonide. Tetrahedron Lett 2002, 43, 47, 8511.
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) 60477 (4S)-2,2-dimethyl-4-[(E)-2-(phenylsulfinyl)ethenyl]-1,3-dioxolane; (E)-2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]ethenyl phenyl sulfoxide C13H16O3S 详情 详情
(II) 60478 (1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(phenylsulfinyl)-1-ethanamine; (1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(phenylsulfinyl)ethylamine C13H19NO3S 详情 详情
(III) 60479 (1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(phenylsulfinyl)-1-ethanamine; (1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(phenylsulfinyl)ethylamine C13H19NO3S 详情 详情
(IV) 60480 (1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(phenylsulfanyl)-1-ethanamine; (1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(phenylsulfanyl)ethylamine C13H19NO2S 详情 详情
(V) 60481 (1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(phenylsulfanyl)-1-ethanamine; (1S)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(phenylsulfanyl)ethylamine C13H19NO2S 详情 详情
(VI) 34785 3-([[(1S,2S)-1-benzyl-3-((4R)-5,5-dimethyl-4-[[(2-methylbenzyl)amino]carbonyl]-1,3-thiazolidin-3-yl)-2-methyl-3-oxopropyl]amino]carbonyl)-2-methylphenyl acetate C35H41N3O5S 详情 详情
(VII) 60482 3-({[(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-(phenylsulfanyl)ethyl]amino}carbonyl)-2-methylphenyl acetate C23H27NO5S 详情 详情
(VIII) 60483 3-[({(1R,2S)-2,3-dihydroxy-1-[(phenylsulfanyl)methyl]propyl}amino)carbonyl]-2-methylphenyl acetate C20H23NO5S 详情 详情
(IX) 13955 (3S,4aS,8aS)-N-(tert-Butyl)decahydro-3-isoquinolinecarboxamide C14H26N2O 详情 详情
Extended Information