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【结 构 式】

【分子编号】25911

【品名】methyl (2S)-3-[[2-((5R)-3-[4-[amino(imino)methyl]phenyl]-4,5-dihydro-5-isoxazolyl)acetyl]amino]-2-[[(3,5-dimethyl-4-isoxazolyl)sulfonyl]amino]propanoate

【CA登记号】

【 分 子 式 】C21H26N6O7S

【 分 子 量 】506.53968

【元素组成】C 49.79% H 5.17% N 16.59% O 22.11% S 6.33%

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:(VII)

The sulfonation of 2(S)-amino-3-(tert-butoxycarbonylamino)propionic acid methyl ester (I) with 3,5-dimethylisoxazol-4-ylsulfonyl chloride (II) by means of triethylamine in dichloromethane gives the corresponding sulfonamide (III), which is deprotected with trifluoroacetic acid yielding the 3-aminopropionic acid derivative (IV). The condensation of (IV) with [3-(4-cyanophenyl)-4,5-dihydroisoxazol-5(R)-yl]acetic acid (V) by means of TBTU and triethylamine in DMF affords the carboxamide (VI). The cyano group of (VI) is treated first with dry HCl and then with NH3, NH4OAc, or CO3(NH4)2 to obtain the amidino group of (VII). Finally, compound (VII) is hydrolyzed with LiOH, 6N HCl, or rabbit liver esterase.

1 Sielecki, T.M.; Olson, R.E.; Wityak, J.; et al.; Orally active isoxazoline glycoprotein IIb/IIIa antagonists with extended duration of action. J Med Chem 1999, 42, 7, 1178.
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) 25095 methyl (2S)-2-amino-3-[(tert-butoxycarbonyl)amino]propanoate C9H18N2O4 详情 详情
(II) 21618 3,5-dimethyl-4-isoxazolesulfonyl chloride 80466-79-1 C5H6ClNO3S 详情 详情
(III) 25912 methyl (2S)-3-[(tert-butoxycarbonyl)amino]-2-[[(3,5-dimethyl-4-isoxazolyl)sulfonyl]amino]propanoate C14H23N3O7S 详情 详情
(IV) 25913 methyl (2S)-3-amino-2-[[(3,5-dimethyl-4-isoxazolyl)sulfonyl]amino]propanoate C9H15N3O5S 详情 详情
(V) 17555 2-[(5R)-3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetic acid C12H10N2O3 详情 详情
(VI) 25910 methyl (2S)-3-([2-[3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetyl]amino)-2-[[(3,5-dimethyl-4-isoxazolyl)sulfonyl]amino]propanoate C21H23N5O7S 详情 详情
(VII) 25911 methyl (2S)-3-[[2-((5R)-3-[4-[amino(imino)methyl]phenyl]-4,5-dihydro-5-isoxazolyl)acetyl]amino]-2-[[(3,5-dimethyl-4-isoxazolyl)sulfonyl]amino]propanoate C21H26N6O7S 详情 详情
Extended Information