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【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%

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:(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
Extended Information