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【结 构 式】

【分子编号】51935

【品名】methyl (2S)-2-[(butoxycarbonyl)amino]-3-([2-[3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetyl]amino)propanoate

【CA登记号】

【 分 子 式 】C21H26N4O6

【 分 子 量 】430.4608

【元素组成】C 58.6% H 6.09% N 13.02% O 22.3%

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:(I)

The reaction of N-(butoxycarbonyl)-3-[2-[3-(4-cyanophenyl)-4,5-dihydroisoxazol-5(R)-yl]acetamido]-L-alanine methyl ester (I) (intermediate (VII) in scheme no. 22467601a) with hydroxylamine and TEA in hot methanol gives the N-hydroxyamidine compound (II), which is treated with Ac2O in acetic acid to yield the N-acetoxyamidino compound (III). The cyclization of (III) by means of Ac2O in refluxing acetic aid affords the 1,2,4-oxadiazole derivative (IV), which is reduced with H2 over Pd/C in methanol/HOAc to provide the amidino derivative (V). Alternatively, the direct reduction of N-acetoxyamidino derivative (III) with H2 over Pd/C in acetic acid also gives the amidino derivative (V). Finally, the methyl ester group of compound (V) is hydrolyzed with LiOH in THF to yield the target roxifiban acetate.

1 Anzalone, L.; Storace, L. Ward, R.; Kauffman, G.S.; Zhang, L.-H.; Ma, P.; The chiral specific synthesis of DMP 754, a platelet GPIIb/IIIa antagonist. Tetrahedron Lett 1996, 37, 26, 4455-8.
2 Confalone, P.N.; Li, H.-Y.; Ma, P. (DuPont Pharmaceuticals Co.); An efficient method for the conversion of nitriles to amidines. WO 9918090 .
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) 51935 methyl (2S)-2-[(butoxycarbonyl)amino]-3-([2-[3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetyl]amino)propanoate C21H26N4O6 详情 详情
(II) 51932 methyl (2S)-3-[[2-(3-[4-[amino(hydroxyimino)methyl]phenyl]-4,5-dihydro-5-isoxazolyl)acetyl]amino]-2-[(butoxycarbonyl)amino]propanoate C21H29N5O7 详情 详情
(III) 51933 methyl (2S)-3-[[2-(3-[4-[[(acetoxy)imino](amino)methyl]phenyl]-4,5-dihydro-5-isoxazolyl)acetyl]amino]-2-[(butoxycarbonyl)amino]propanoate C23H31N5O8 详情 详情
(IV) 51934 methyl (2S)-2-[(butoxycarbonyl)amino]-3-[(2-[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-4,5-dihydro-5-isoxazolyl]acetyl)amino]propanoate C23H29N5O7 详情 详情
(V) 51936 methyl (2S)-3-[[2-(3-[4-[amino(imino)methyl]phenyl]-4,5-dihydro-5-isoxazolyl)acetyl]amino]-2-[(butoxycarbonyl)amino]propanoate C21H29N5O6 详情 详情
Extended Information