新产品编号:278941
(R)-2-氨基-N-苄基-3-甲氧基丙酰胺Chemical Name: 2(R)-Amino-N-benzyl-3-methoxypropionamide; N1-Benzyl-O-methyl-D-serinamide
CAS No. 196601-69-1
项目整合开发状态: Preclinical
项目研究机构: Research Corporation Technologies (Technology Transfer), National Institutes of Health (Originator), University of Houston (Originator)
合成路线:D-Serine (I) was protected as the N-benzyloxycarbonyl derivative (II) by means of benzyl chloroformate in the presence of MgO.Methylation of the alcohol hydroxyl of (II) under Williamson conditions using iodomethane and Ag2O also produced esterification of the carboxyl group to give (III),which was further hydrolyzed to carboxylic acid (IV) with K2CO3 in MeOH-H2O.After activation of (IV) as the mixed anhydride with isobutyl chloroformate,coupling with benzyl amine furnished amide (V).This was alternatively obtained through a related procedure involving coupling of N-Cbz-serine (II) with benzylamine,followed by O-methylation of the resulting hydroxy amide (VI) with iodomethane and Ag2O.Finally,the N-carbobenzoxy protecting group of (V) was removed by catalytic hydrogenolysis in the presence of Pd/C.
📌 参考资料/链接：
参考文献标题:Anticonvulsant enantiomeric amino acid derivs.
文献作者:Kohn,H.; Andurkar,S.V.(Research Corporation Technologies,Inc.)
参考来源:US 6048899; WO 0000463
📄 详细内容
合成路线:D-Serine (I) was protected as the N-benzyloxycarbonyl derivative (II) by means of benzyl chloroformate in the presence of MgO.Methylation of the alcohol hydroxyl of (II) under Williamson conditions using iodomethane and Ag2O also produced esterification of the carboxyl group to give (III),which was further hydrolyzed to carboxylic acid (IV) with K2CO3 in MeOH-H2O.After activation of (IV) as the mixed anhydride with isobutyl chloroformate,coupling with benzyl amine furnished amide (V).This was alternatively obtained through a related procedure involving coupling of N-Cbz-serine (II) with benzylamine,followed by O-methylation of the resulting hydroxy amide (VI) with iodomethane and Ag2O.Finally,the N-carbobenzoxy protecting group of (V) was removed by catalytic hydrogenolysis in the presence of Pd/C.
参考文献标题:Synthesis and anticonvulsant activities of (R)-(O)-methylserine derivatives
文献作者:Andurkar,S.V.; et al.
参考来源:Tetrahedron Asymmetry 1998,9(21),3841
产品链接: CAS No. 196601-69-1››