Tetrahedron: Asymmetry

Synthesis and anticonvulsant activities of (R)-(O)-methylserine derivatives

SV Andurkar, JP Stables, H Kohn

Index: Andurkar, Shridhar V.; Stables, James P.; Kohn, Harold Tetrahedron Asymmetry, 1998 , vol. 9, # 21 p. 3841 - 3854

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Citation Number: 29

Abstract

Efficient procedures for the synthesis of (R)-N-benzyl-2-amino-3-methoxypropionamide ((R)- 3), 2-acetamido-3-methoxypropionic acid (4), and O-methylserine (5) are described beginning from (R)-Cbz-serine ((R)-7). The reactions proceeded with little or no racemization and permitted the synthesis of the potent anticonvulsant (R)-N-benzyl-2- acetamido-3-methoxypropionamide ((R)-2). The anticonvulsant activities of 2–4 were ...