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【结 构 式】

【分子编号】28135

【品名】methyl 2-[3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetate

【CA登记号】

【 分 子 式 】C13H12N2O3

【 分 子 量 】244.24996

【元素组成】C 63.93% H 4.95% N 11.47% O 19.65%

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:(VIII)

Oxime (VI) was prepared from 4-cyanobenzaldehyde (V) upon treatment with hydroxylamine-HCl and pyridine. The nitrile oxide generated from oxime (VI) and NaOCl underwent a dipolar cycloaddition to methyl butenoate (VII) to produce the racemic isoxazoline (VIII). After conversion of the nitrile group of (VIII) to imidate (IX), reaction with methanolic ammonia yielded amidine (X), which was protected with Boc2O to give (XI). Hydrolysis of the methyl ester of (XI) with LiOH provided carboxylic acid (XII), which was coupled to amine (IV) using TBTU to afford amide (XIII) as a diasteromeric mixture. After Boc group removal by acidic treatment yielding (XIV), its methyl ester group was hydrolyzed with LiOH to afford the corresponding acid. The diastereomeric mixture of carboxylic acids was finally separated by preparative chiral HPLC.

1 Wityak, J.; Xue, C.-B.; Sielecki-Dzurdz, T.M.; Olson, R.E.; Degrado, W.F.; Cain, G.A. (DuPont Pharmaceuticals Co.); Novel isoxazoline and isoxazole fibrinogen receptor antagonists. EP 0730590; EP 0832076; JP 1997505590; JP 1999504651; US 5849736; WO 9514683; WO 9638426 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 28133 methyl (2S)-3-amino-2-[[(3-methylphenyl)sulfonyl]amino]propanoate C11H16N2O4S 详情 详情
(V) 17552 4-formylbenzonitrile; 4-Cyanobenzaldehyde 105-07-7 C8H5NO 详情 详情
(VI) 17553 4-[(hydroxyimino)methyl]benzonitrile C8H6N2O 详情 详情
(VII) 28134 methyl 3-butenoate C5H8O2 详情 详情
(VIII) 28135 methyl 2-[3-(4-cyanophenyl)-4,5-dihydro-5-isoxazolyl]acetate C13H12N2O3 详情 详情
(IX) 28136 methyl 2-(3-[4-[imino(methoxy)methyl]phenyl]-4,5-dihydro-5-isoxazolyl)acetate C14H16N2O4 详情 详情
(X) 28137 methyl 2-(3-[4-[amino(imino)methyl]phenyl]-4,5-dihydro-5-isoxazolyl)acetate C13H15N3O3 详情 详情
(XI) 28138 methyl 2-[3-(4-[amino[(tert-butoxycarbonyl)imino]methyl]phenyl)-4,5-dihydro-5-isoxazolyl]acetate C18H23N3O5 详情 详情
(XII) 28139 2-[3-(4-[amino[(tert-butoxycarbonyl)imino]methyl]phenyl)-4,5-dihydro-5-isoxazolyl]acetic acid C17H21N3O5 详情 详情
(XIII) 28140 methyl (2S)-3-[[2-(3-[4-[[(tert-butoxycarbonyl)amino](imino)methyl]phenyl]-4,5-dihydro-5-isoxazolyl)acetyl]amino]-2-[[(3-methylphenyl)sulfonyl]amino]propanoate C28H35N5O8S 详情 详情
(XIV) 28141 methyl (2S)-3-[[2-(3-[4-[amino(imino)methyl]phenyl]-4,5-dihydro-5-isoxazolyl)acetyl]amino]-2-[[(3-methylphenyl)sulfonyl]amino]propanoate C23H27N5O6S 详情 详情
Extended Information