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【结 构 式】 
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【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% |
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 |