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【结 构 式】

【分子编号】60819

【品名】tert-butyl 2-[(allyloxy)imino]-3-(3,4-dichlorophenyl)-5-hydroxypentyl(methyl)carbamate

【CA登记号】

【 分 子 式 】C20H28Cl2N2O4

【 分 子 量 】431.3588

【元素组成】C 55.69% H 6.54% Cl 16.44% N 6.49% O 14.84%

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:(XIII)

Claisen condensation between 3,4-dichlorophenylacetic acid (VI) and N-Boc-sarcosine methyl ester (VII), followed by acidic decarboxylation of the intermediate keto acid, furnishes amino ketone (VIII). Alkylation of (VIII) with the silylated bromoethanol (IX) in the presence of NaH and NaI yields adduct (X). Subsequent condensation of ketone (X) with O-allyl hydroxylamine (XI) generates the corresponding oxime (XII). After desilylation of (XII) with tetrabutylammonium fluoride, the resultant primary alcohol (XIII) is oxidized under Swern conditions to furnish aldehyde (XIV)

1 Carruthers, N.I.; Alaimo, C.A.; Shih, N.-Y.; Lavey, B.J.; Ting, P.C.; Reichard, G.A. (Schering Corp.); Substd. oximes as neurokinin antagonists. EP 1032561; WO 9926924 .
2 Carruthers, N.I.; Reichard, G.A.; Shih, N.-Y.; Lavey, B.J.; Alaimo, C.A.; Ting, P.C. (Schering Corp.); Substd. oximes as neurokinin antagonists. US 6063926 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 30414 2-(3,4-dichlorophenyl)acetic acid;2-(3,4-Dichlorophenyl)acetic acid 5807-30-7 C8H6Cl2O2 详情 详情
(VII) 60815 methyl 2-[(tert-butoxycarbonyl)(methyl)amino]acetate C9H17NO4 详情 详情
(VIII) 60816 tert-butyl 3-(3,4-dichlorophenyl)-2-oxopropyl(methyl)carbamate C15H19Cl2NO3 详情 详情
(IX) 55573 2-Bromoethoxy-t-butyldimethylsilane 86864-60-0 C8H19BrOSi 详情 详情
(X) 60817 tert-butyl 5-{[tert-butyl(dimethyl)silyl]oxy}-3-(3,4-dichlorophenyl)-2-oxopentyl(methyl)carbamate C23H37Cl2NO4Si 详情 详情
(XI) 49195 3-(aminooxy)-1-propene; O-allylhydroxylamine C3H7NO 详情 详情
(XII) 60818 tert-butyl 2-[(allyloxy)imino]-5-{[tert-butyl(dimethyl)silyl]oxy}-3-(3,4-dichlorophenyl)pentyl(methyl)carbamate C26H42Cl2N2O4Si 详情 详情
(XIII) 60819 tert-butyl 2-[(allyloxy)imino]-3-(3,4-dichlorophenyl)-5-hydroxypentyl(methyl)carbamate C20H28Cl2N2O4 详情 详情
(XIV) 60820 tert-butyl 2-[(allyloxy)imino]-3-(3,4-dichlorophenyl)-5-oxopentyl(methyl)carbamate C20H26Cl2N2O4 详情 详情
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