【结 构 式】 |
【分子编号】34939 【品名】ethyl 2-[6-([4-[[(tert-butoxycarbonyl)amino](imino)methyl]-2-fluorobenzoyl]amino)-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl]acetate 【CA登记号】 |
【 分 子 式 】C27H30FN3O6 【 分 子 量 】511.5502232 【元素组成】C 63.39% H 5.91% F 3.71% N 8.21% O 18.77% |
合成路线1
该中间体在本合成路线中的序号:(V)The known amino tetralone (I) was coupled with 4-cyano-2-fluorobenzoic acid (II) in the presence of EDC to give amide (III). Subsequent conversion of the nitrile group of (III) into the required amidine was achieved by the following sequence consisting of addition of SH2, followed by S-methylation to produce the iminothioether (IV), displacement of the methylthio group of (IV) with ammonium acetate, and then protection of the resulting amidine with di-tert-butyl dicarbonate, yielding the Boc-protected amidine (V). Basic hydrolysis of the ethyl ester group of (V) generated the corresponding carboxylic acid (VI). Finally, the Boc protecting group of (VI) was cleaved by means of trifluoroacetic acid.
【1】 Fisher, M.J.; Harms, C.S.; Giese, U.; et al.; Fused bicyclic Gly-Asp beta-turn mimics with potent affinity for GPIIb-IIIa. Exploration of the arginine isostere. Bioorg Med Chem Lett 2000, 10, 4, 385. |
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) | 34936 | ethyl 2-(6-amino-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl)acetate | C14H17NO3 | 详情 | 详情 | |
(II) | 28090 | 4-cyano-2-fluorobenzoic acid | C8H4FNO2 | 详情 | 详情 | |
(III) | 34937 | ethyl 2-[6-[(4-cyano-2-fluorobenzoyl)amino]-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl]acetate | C22H19FN2O4 | 详情 | 详情 | |
(IV) | 34938 | ethyl 2-[6-([2-fluoro-4-[imino(methylsulfanyl)methyl]benzoyl]amino)-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl]acetate | C23H23FN2O4S | 详情 | 详情 | |
(V) | 34939 | ethyl 2-[6-([4-[[(tert-butoxycarbonyl)amino](imino)methyl]-2-fluorobenzoyl]amino)-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl]acetate | C27H30FN3O6 | 详情 | 详情 | |
(VI) | 34940 | 2-[6-([4-[[(tert-butoxycarbonyl)amino](imino)methyl]-2-fluorobenzoyl]amino)-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl]acetic acid | C25H26FN3O6 | 详情 | 详情 |