Reaction of 4-Bromoalkyl-4-methoxy-2,5-oxazolidione with Alcohol or a-Amino Acid Ester and Transformation of the Products

Reaction of N-carboxy a-dehydroamino acid anhydride with methanol in the presence of NBS gave 4-bromoalkyl-4-methoxy-2,5- oxazolidione, which was further treated with alcohol or a-amino acid ester to give extremely different two types of products, 2-oxaaolinone and a-(oximino)acyl-a-amino acid derivatives respectively.In a previous paper, we reported briefly that the reaction of N-carboxy adehydroamino acid anhydride (ANCA; L)l with methanol in the presence of N- bromosuccinimide (NBS) gave the versatile methyl 5-alkyl-2-oxazolinone-4carboxylate (3) v & 4-bromoalkyl-4-methoxy-2.5-oxazolidione (2) by two steps.2