Dimethylformamide → HCID 14672925, compound

Participants

Reaction Steps

18.5 g of 2-oxo-1 pyrrolidinyl acetic acid was dissolved in 500 ml of dimethylformamide and the solution was cooled to -15° C., to which 18.53 g of isobutyl chloroformate was added and 13.21 g of triethylamine was added dropwise at -15° to 5° C. After stirring at -10° to -5° C. for 15 minutes, 17.04 g of glycine methyl hydrochloride was added and 13.73 g of triethylamine was added dropwise at -10° to -5° C. The reaction liquid was allowed to stand so as to rise its temperature to room temperature over 2 hours and triethylamine hydrochloride was filtered off. Dimethylformamide was distilled off under reduced pressure and the residue was purified through the chromatography on silica gel (silica gel 500 g, chloroform-1 to 2 % of methanol as the eluent). Then, the solvent was distilled off to obtain 17.97 g of N- [ (2-oxo-1-pyrrolidinyl)acetyl]glycine methyl ester as the oily substance. This was dissolved in 100 ml of methanol and the solution of 4.78 g of sodium hydroxide dissolved in 150 ml of methanol was added thereto and reacted at room temperature for 12 hours. After 10 g of acetic acid was added, methanol was distilled off under reduced pressure and the residue was purified through the chromatography on silica gel (silica gel 340 g, chloroform-10 % of methanol-1 % of formic acid as the eluent). The solvent was distilled off and the residue was crystallized from tetrahydrofuran to obtain the titled compound.

Provenance & Evidence