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【结 构 式】

【分子编号】23587

【品名】N-[(1S,2S,3S,5R)-6,6-dimethyl-2-(2-oxoethyl)bicyclo[3.1.1]hept-3-yl]-2,2,2-trifluoroacetamide

【CA登记号】

【 分 子 式 】C13H18F3NO2

【 分 子 量 】277.2866696

【元素组成】C 56.31% H 6.54% F 20.55% N 5.05% O 11.54%

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:(XIX)

2) Amine (IX) is acylated with trifluoroacetic anhydride and pyridine in dichloromethane to the amide (XVII), which is hydrolyzed with p-toluenesulfonic acid in methanol yielding the alcohol (XVIII). The oxidation of (XVIII) with anhydrous H2SO4 - pyridine in DMSO triethylamine affords the aldehyde (XIX), which is submitted to a Wittig condensation with 4-carboxybutyltriphenylphosphonium bromide by means of NaH in DMSO giving the heptenoic acid (XX). Methylation of (XX) with diazomethane affords the corresponding methyl ester (XXI), which is deprotected with NaOH yielding the amino ester (XXII). The acylation of (XXII) with the acyl chloride (X) gives the protected amido ester (XXIII), which by partial hydrolysis with NaOH affords the racemic mixture (XVI), already obtained.

1 Kawasaki, A.; Miyake, H.; Okegawa, T. (Ono Pharmaceutical Co., Ltd.); 13-Aza-14-oxo-TXA2 analogues. AU 8543495; EP 0171146; ES 8704880; ES 8705370; JP 1989151545; US 4792550 .
2 Castaner, J.; Prous, J.; ONO-3708. Drugs Fut 1987, 12, 5, 446.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IX) 23577 (1S,2S,3S,5R)-6,6-dimethyl-2-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]bicyclo[3.1.1]heptan-3-amine; (1S,2S,3S,5R)-6,6-dimethyl-2-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]bicyclo[3.1.1]hept-3-ylamine C17H31NO2 详情 详情
(X) 23578 2-chloro-1-cyclopentyl-2-oxoethyl pivalate C12H19ClO3 详情 详情
(XIV) 23582 (4-carboxybutyl)(triphenyl)phosphonium C23H24O2P 详情 详情
(XVI) 23584 (Z)-7-[(1S,2S,3S,5R)-3-[(2-cyclopentyl-2-hydroxyacetyl)amino]-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-5-heptenoic acid C23H37NO4 详情 详情
(XVII) 23585 N-[(1S,2S,3S,5R)-6,6-dimethyl-2-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]bicyclo[3.1.1]hept-3-yl]-2,2,2-trifluoroacetamide C19H30F3NO3 详情 详情
(XVIII) 23586 2,2,2-trifluoro-N-[(1S,2S,3S,5R)-2-(2-hydroxyethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-yl]acetamide C13H20F3NO2 详情 详情
(XIX) 23587 N-[(1S,2S,3S,5R)-6,6-dimethyl-2-(2-oxoethyl)bicyclo[3.1.1]hept-3-yl]-2,2,2-trifluoroacetamide C13H18F3NO2 详情 详情
(XX) 23588 (Z)-7-[(1S,2S,3S,5R)-6,6-dimethyl-3-[(2,2,2-trifluoroacetyl)amino]bicyclo[3.1.1]hept-2-yl]-5-heptenoic acid C18H26F3NO3 详情 详情
(XXI) 23589 (Z)-7-[(1S,2S,5R)-6,6-dimethyl-3-[(2,2,2-trifluoroacetyl)amino]bicyclo[3.1.1]hept-2-yl]-5-heptenoic acid C18H26F3NO3 详情 详情
(XXII) 23590 (Z)-7-[(1S,2S,3S,5R)-3-amino-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-5-heptenoic acid C16H27NO2 详情 详情
(XXIII) 23591 methyl (Z)-7-[(1S,2S,3S,5R)-3-[(2-cyclopentyl-2-hydroxyacetyl)amino]-6,6-dimethylbicyclo[3.1.1]hept-2-yl]-5-heptenoate C24H39NO4 详情 详情
Extended Information