• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】28643

【品名】benzyl (2R)-2-(benzylamino)-4-methylpentanoate

【CA登记号】

【 分 子 式 】C20H25NO2

【 分 子 量 】311.42404

【元素组成】C 77.14% H 8.09% N 4.5% O 10.27%

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)

The esterification of D-leucine (I) with benzyl alcohol and HCl gives the corresponding ester (II), which is N-benzylated by reductocondensation with benzaldehyde and sodium cyanoborohydride yielding N-benzyl-D-leucine benzyl ester (III). The condensation of (III) with methyl phenyl phosphinyl chloride (IV) by means of N-methylmorpholine in dichloromethane affords the phosphinylamino derivative (V), which is treated with H2 over Pd/C in methanol to give N-benzyl-N-[methyl(phenyl)phosphinyl]-D-leucine (VI). The condensation of (VI) with O-benzylhydroxylamine (VII) by means of 1-[3-(dimethylamino) propyl]-3-ethylcarbodiimide (DEC) and HOBT in DMF yields the N-benzyl hydroxamic acid (VIII) as a diastereomeric mixture that is separated by flash chromatography providing the diastereomer (IX). Finally, this compound is deprotected by hydrogenation with H2 over Pd/C in methanol.

1 Elst, L.V.; et al.; A multinuclear MR study of Gd-EOB-DTPA: Comprehensive preclinical characterization of an organ specific MRI contrast agent. Magn Reson Med 1997, 38, 4, 604.
2 Taiwo, Y.O.; Pikul, S.; De, B.; McDow-Dunham, K.L. (The Procter & Gamble Co.); Phosphinic acid amides as matrix metalloprotease inhibitors. US 5830915; WO 9808853 .
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) 16010 D-leucine 328-38-1 C6H13NO2 详情 详情
(II) 28648 benzyl (2R)-2-amino-4-methylpentanoate C13H19NO2 详情 详情
(III) 28643 benzyl (2R)-2-(benzylamino)-4-methylpentanoate C20H25NO2 详情 详情
(IV) 28644 methyl(phenyl)phosphinic chloride 5761-97-7 C7H8ClOP 详情 详情
(V) 28645 benzyl (2R)-2-[benzyl[methyl(phenyl)phosphoryl]amino]-4-methylpentanoate C27H32NO3P 详情 详情
(VI) 28646 (2R)-2-[benzyl[methyl(phenyl)phosphoryl]amino]-4-methylpentanoic acid C20H26NO3P 详情 详情
(VII) 14640 O-benzylhydroxylamine; 1-[(aminooxy)methyl]benzene 622-33-3 C7H9NO 详情 详情
(VIII) 28647 (2R)-2-[benzyl[methyl(phenyl)phosphoryl]amino]-N-(benzyloxy)-4-methylpentanamide C27H33N2O3P 详情 详情
(IX) 28649 (2R)-2-[benzyl[methyl(phenyl)phosphoryl]amino]-N-(benzyloxy)-4-methylpentanamide C27H33N2O3P 详情 详情
Extended Information