【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% |
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 |