L-α-Tosylamido-β-propiolactoneの反応(第3報) : メルカプタン類との反応

Abstract

The reaction of mercaptans with L-α-tosylamido-β-propiolactone (I) derived from L-asparagine was investigated. In the presence of one molar equivalent of alkali, I reacted with mercaptans to afford N-tosyl-L-serine (III) or methyl ester (IV) of III in aqueous THF solution or methanolic solution, respectively. However, by adding catalytic amount of alkali, L-α-tosylamido-β-hydroxypropionic acid thioester (V) was obtained from the reaction mixture of I and mercaptans in THF or aqueous THF solution. No reaction was observed when I was treated with mercaptans in the presence or absence of acid catalyst.