N-carbobenzyloxyalanine → 1-[N-benzyloxycarbonyl-(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(R)-carboxylic acid, ethyl ester

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Reaction Steps

To a solution of ethyl hexahydrofuro[3,4-b]pyrrole-2-carboxylate in ethyl acetate add N-benzyloxycarbonyl-(S)-alanine, N-hydroxysuccinimide ester. Stir the reaction mixture at room temperature for 20 hours and concentrate it in vacuo. Place the residue on a column of silica gel (3000 g, 60-200 mesh) and elute with chloroform: ethyl acetate 10:1 to give 1-[N-benzyloxycarbonyl-(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(R)-carboxylic acid, ethyl ester, and 1-[N-benzyloxycarbonyl(S)-alanyl]hexahydrofuro[3,4-b]pyrrole-2(S)-carboxylic acid, ethyl ester.

Provenance & Evidence