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【结 构 式】

【分子编号】49842

【品名】methyl (2S)-3-[(tert-butoxycarbonyl)amino]-2-[[(2-methylphenyl)sulfonyl]amino]propanoate

【CA登记号】

【 分 子 式 】C16H24N2O6S

【 分 子 量 】372.44244

【元素组成】C 51.6% H 6.5% N 7.52% O 25.77% S 8.61%

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:(III)

Condensation of methyl N3-Boc-2,3-diaminopropionate (I) with o-tolylsulfonyl chloride (II) produced sulfonamide (III). Subsequent acid cleavage of the Boc protecting group of (III) gave amine (IV). Coupling of amine (IV) with the previously described (R)-oxazolidineacetic acid (V) using TBTU afforded amide (VI). Pinner reaction of (VI) with methanolic HCl converted nitrile (VI) into imidate (VII), which was further treated with ammonium acetate to furnish amidine (VIII). Finally, selective hydrolysis of the ester function of (VIII) was achieved with either LiOH or with an enzymatic method using rabbit liver esterase.

1 Sielecki, T.M.; et al.; Synthesis and pharmacology of modified amidine isoxazoline glycoprotein IIb/IIIa receptor antagonists. Bioorg Med Chem Lett 2001, 11, 16, 2201.
2 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) 49841 o-Toluenesulfonyl Chloride 133-59-5 C7H7ClO2S 详情 详情
(III) 49842 methyl (2S)-3-[(tert-butoxycarbonyl)amino]-2-[[(2-methylphenyl)sulfonyl]amino]propanoate C16H24N2O6S 详情 详情
(IV) 49843 methyl (2S)-3-amino-2-[[(2-methylphenyl)sulfonyl]amino]propanoate C11H16N2O4S 详情 详情
(V) 17555 2-[(5R)-3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetic acid C12H10N2O3 详情 详情
(VI) 49844 methyl (2S)-3-([2-[(5R)-3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetyl]amino)-2-[[(2-methylphenyl)sulfonyl]amino]propanoate C23H24N4O6S 详情 详情
(VII) 49845 methyl (2S)-3-[[2-((5R)-3-[4-[imino(methoxy)methyl]phenyl]-4,5-dihydro-5-isoxazolyl)acetyl]amino]-2-[[(2-methylphenyl)sulfonyl]amino]propanoate C24H28N4O7S 详情 详情
(VIII) 49846 methyl (2S)-3-[[2-((5R)-3-[4-[amino(imino)methyl]phenyl]-4,5-dihydro-5-isoxazolyl)acetyl]amino]-2-[[(2-methylphenyl)sulfonyl]amino]propanoate C23H27N5O6S 详情 详情
Extended Information