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【结 构 式】

【药物名称】

【化学名称】2(R)-Amino-N-benzyl-3-methoxypropionamide
      N1-Benzyl-O-methyl-D-serinamide

【CA登记号】196601-69-1

【 分 子 式 】C11H16N2O2

【 分 子 量 】208.26237

【开发单位】Research Corporation Technologies (Technology Transfer), National Institutes of Health (Originator), University of Houston (Originator)

【药理作用】Antiepileptic Drugs, NEUROLOGIC DRUGS

合成路线1

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.

1 Andurkar, S.V.; et al.; Synthesis and anticonvulsant activities of (R)-(O)-methylserine derivatives. Tetrahedron Asymmetry 1998, 9, 21, 3841.
2 Kohn, H.; Andurkar, S.V. (Research Corporation Technologies, Inc.); Anticonvulsant enantiomeric amino acid derivs.. US 6048899; WO 0000463 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10101 Benzyloxycarbonyl chloride; Benzyl chloroformate; 1-[[(Chlorocarbonyl)oxy]methyl]benzene 501-53-1 C8H7ClO2 详情 详情
15147 Benzylamine; Phenylmethanamine 100-46-9 C7H9N 详情 详情
(I) 15728 (+)-2-Amino-3-hydroxypropionic acid; D-(+)-Serine; D-serine 312-84-5 C3H7NO3 详情 详情
(II) 32794 (2S)-2-[[(benzyloxy)carbonyl]amino]-3-hydroxypropionic acid C11H13NO5 详情 详情
(III) 38794 methyl (2R)-2-[[(benzyloxy)carbonyl]amino]-3-methoxypropanoate C13H17NO5 详情 详情
(IV) 38795 (2R)-2-[[(benzyloxy)carbonyl]amino]-3-methoxypropionic acid C12H15NO5 详情 详情
(V) 38796 benzyl (1R)-2-(benzylamino)-1-(methoxymethyl)-2-oxoethylcarbamate C19H22N2O4 详情 详情
(VI) 38797 benzyl (1R)-2-(benzylamino)-1-(hydroxymethyl)-2-oxoethylcarbamate C18H20N2O4 详情 详情
Extended Information