methyl (2S)-3-([2-[(5R)-3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetyl]amino)-2-[[(2-methylphenyl)sulfonyl]amino]propanoate -Drug Synthesis Database

【结构式】

【分子编号】49844

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

【CA登记号】

【分子式】C₂₃H₂₄N₄O₆S

【分子量】484.53292

【元素组成】C 57.01% H 4.99% N 11.56% O 19.81% S 6.62%

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：(VI)

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.

参考文献中间体

合成目标

【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