【结 构 式】 |
【分子编号】23900 【品名】ethyl 3-oxo-5-(trimethylsilyl)-4-pentynoate 【CA登记号】 |
【 分 子 式 】C10H16O3Si 【 分 子 量 】212.32074 【元素组成】C 56.57% H 7.6% O 22.61% Si 13.23% |
合成路线1
该中间体在本合成路线中的序号:(V)A short and efficient synthesis of xemilofiban has been achieved as follows: The reaction of ethyl chloroformate (I) with trimethylsilylacetylene (II) by means of butyllithium gives ethyl 3-(trimethylsilyl)propyonate (III), which is condensed with the lithium salt of ethyl acetate (IV) yielding ethyl 5-(trimethylsilyl)-3-oxo-4-pentynoate (V). The selective reduction of (V) with lyophilized baker's yeast (Saccharomyces cerevisiae, Sigma type II) affords ethyl 3(R)-hydroxy-5-(trimethylsilyl)-4-pentynoate (VI), which by reaction with ammonia (VII), diethyl azodicarboxylate (VIII) and triphenylphosphine, followed by hydrolysis with water gives 3(S)-amino-5-(trimethylsilyl)-4-pentynoate (IX). Finally, this compound is condensed with N-(4-amidinophenyl)succinamic acid (XI) by means of isobutyl chloroformate and N-methylmorpholine (NMM). The intermediate succinamic acid (XI) has been obtained by condensation of 4-aminobenzamidine (XII) with succinic anhydride (XIII) in DMF.
【1】 Cossy, J.; Schmitt, A.; Cinquin, C.; Buisson, D.; Belotti, D.; A very short, efficient and inexpensive synthesis of the prodrug form of SC-54701A a platelet aggregation inhibitor. Bioorg Med Chem Lett 1997, 7, 13, 1699. |
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) | 11229 | 1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate | 541-41-3 | C3H5ClO2 | 详情 | 详情 |
(II) | 23897 | ethynyl(trimethyl)silane;trimethylsilyl acetylene | 1066-54-2 | C5H10Si | 详情 | 详情 |
(III) | 23898 | ethyl 3-(trimethylsilyl)-2-propynoate | 29394-58-9 | C8H14O2Si | 详情 | 详情 |
(IV) | 23899 | lithium 1-ethoxy-1-ethylenolate | C4H7LiO2 | 详情 | 详情 | |
(V) | 23900 | ethyl 3-oxo-5-(trimethylsilyl)-4-pentynoate | C10H16O3Si | 详情 | 详情 | |
(VI) | 23901 | ethyl (3R)-3-hydroxy-5-(trimethylsilyl)-4-pentynoate | C10H18O3Si | 详情 | 详情 | |
(VIII) | 20989 | Diethylazadicarboxylate; Diethyl Azodiformate; Azodiformic Acid Diethyl Ester; Diethyl Azodicarboxylate; Azodicarboxylic Acid Diethyl Ester; Diethyl 1,2-diazenedicarboxylate | 1972-28-7 | C6H10N2O4 | 详情 | 详情 |
(IX) | 23904 | ethyl (3S)-3-amino-5-(trimethylsilyl)-4-pentynoate | C10H19NO2Si | 详情 | 详情 | |
(X) | 16297 | ethyl (3S)-3-amino-4-pentynoate | C7H11NO2 | 详情 | 详情 | |
(XI) | 16296 | 4-[4-[amino(imino)methyl]anilino]-4-oxobutyric acid | C11H13N3O3 | 详情 | 详情 | |
(XII) | 16295 | 4-aminobenzenecarboximidamide hydrochloride; 4-aminobenzamidine | 3858-83-1 | C7H9N3 | 详情 | 详情 |
(XIII) | 11291 | Dihydro-2,5-furandione; Succinic anhydride | 108-30-5 | C4H4O3 | 详情 | 详情 |