N-carbobenzyloxyalanine → HCID 67788511, compound

Participants

Reaction Steps

To a solution of 10.0 g of ethyl octahydroindole-2-carboxylate (prepared in as shown in paragraph A of this example) in 400 ml of ethyl acetate add 17.0 g of 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]octahydroindole-2(R)-carboxylic acid, ethyl ester, a colorless oil [α]D26 +22.0° (ethanol) and 1-[N-benzyloxycarbonyl-(S)alanyl]octahydroindole-2(S)-carboxylic acid, ethyl ester, a colorless oil [α]D26 -96.4° (ethanol).

Provenance & Evidence