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【结 构 式】

【分子编号】36899

【品名】ethyl 2-[6-([4-[imino(methylsulfanyl)methyl]benzoyl]amino)-3,4-dihydro-2H-chromen-2-yl]acetate

【CA登记号】

【 分 子 式 】C22H24N2O4S

【 分 子 量 】412.50964

【元素组成】C 64.06% H 5.86% N 6.79% O 15.51% S 7.77%

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:(IX)

Hydrogenation of 6-nitrocoumarin (I) in the presence of Pd/C and di-tert-butyl dicarbonate provided (II). Partial reduction of the lactone function of (II) with DIBAL at low temperature gave rise to lactol (III), which was submitted to a Wittig condensation with (ethoxycarbonyl)triphenylphosphorane (IV) yielding chromaneacetic acid ethyl ester (V). The Boc protecting group of (V) was then removed with trifluoroacetic acid to afford aniline (VI), which was acylated with 4-cyanobenzoic acid (VII) in the presence of EDC to give amide (VIII). Addition of H2S to the nitrile group of (VIII), followed by S-methylation provided (IX). Then, displacement of the methylthio group of (IX) by ammonium acetate and further treatment with di-tert-butyl dicarbonate yielded the Boc-protected benzamidine (X). Finally, Boc-deprotection with trifluoroacetic acid furnished the title amidino ester.

1 Fisher, M.J.; Arfstan, A.E.; Giese, U.; et al.; Fused bicyclic Gly-Asp beta-turn mimics with specific affinity for GPIIb-IIIa. J Med Chem 1999, 42, 23, 4875.
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) 36892 6-nitro-2H-chromen-2-one 2725-81-7 C9H5NO4 详情 详情
(II) 36893 tert-butyl 2-oxo-3,4-dihydro-2H-chromen-6-ylcarbamate C14H17NO4 详情 详情
(III) 36894 tert-butyl 2-hydroxy-3,4-dihydro-2H-chromen-6-ylcarbamate C14H19NO4 详情 详情
(IV) 14182 ethyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate; (Carbethoxymethylene)triphenylphosphorane 1099-45-2 C22H21O2P 详情 详情
(V) 36895 ethyl 2-[6-[(tert-butoxycarbonyl)amino]-3,4-dihydro-2H-chromen-2-yl]acetate C18H25NO5 详情 详情
(VI) 36896 ethyl 2-(6-amino-3,4-dihydro-2H-chromen-2-yl)acetate C13H17NO3 详情 详情
(VII) 36897 4-cyanobenzoic acid;4-Carboxybenzonitrile;p-Carboxybenzonitrile 619-65-8 C8H5NO2 详情 详情
(VIII) 36898 ethyl 2-[6-[(4-cyanobenzoyl)amino]-3,4-dihydro-2H-chromen-2-yl]acetate C21H20N2O4 详情 详情
(IX) 36899 ethyl 2-[6-([4-[imino(methylsulfanyl)methyl]benzoyl]amino)-3,4-dihydro-2H-chromen-2-yl]acetate C22H24N2O4S 详情 详情
(X) 36900 ethyl 2-[6-([4-[[(tert-butoxycarbonyl)amino](imino)methyl]benzoyl]amino)-3,4-dihydro-2H-chromen-2-yl]acetate C26H31N3O6 详情 详情
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