Methyl chloroformate → HCID 21993429, compound

Participants

Reaction Conditions

Reaction Steps

4.3 g (30 mmol) of 3-cyclobutyl-DL-alanine [A. Burger et al., J. Med. Chem. 6, 221 (1963)] is dissolved in 15 ml of 2M NaOH solution, cooled to 0° C. and simultaneously 16.5 ml of 2M NaOH solution and 2.55 ml (33 mmol) of methyl chloroformate are added with vigorous stirring. Stirring is continued at this temperature for 30 minutes and at room temperature for 2 hours. The reaction mixture is diluted with 40 ml of water, extracted with 10 ml of diethyl ether, then acidified to pH3 with 3M HCl. The product is extracted with ethyl acetate (4×20 ml), the extracts are pooled, washed with 20 ml of water, dried over anhydrous sodium sulphate and evaporated at a pressure of 2.0-2.5 kPa. The oily residue [5.3 g (88%), Rf(7)=0.61] is used without further purification in the next step.

Provenance & Evidence