4-Chloroaniline → Alanine, N-((p-chlorophenyl)carbamoyl)-2-methyl-, methyl ester

Participants

Reaction Steps

A solution of 17.0 g (119 mmol) of 2-isocyanato-2-methylpropionic acid methyl ester in 150 ml of absolute tetrahydrofuran was added, over a 15 minute period to 15.1 g (119 mmol) of p-chloroaniline in 300 ml of absolute tetrahydrofuran. After refluxing the mixture for three days, the solution was evaporated to dryness. The product, after two recrystallizations from methylene chloride, was dried for 6 hours at 40° C., under greatly reduced pressure, to yield N-[(4-chlorophenyl)-carbamoyl]-2-methylalanine methyl ester, m.p. 147°-148° C.

Provenance & Evidence