Triethylamine → HCID 14672925, compound

Temperature

-8 °C

55 g of (2-oxo-1-pyrrolidinyl)acetic acid was dissolved in 1 l of dimethylformamide and 39.3 g of triethylamine was added thereto. After the solution was cooled to -8° C., 55.1 g of isobutyl chloroformate was added at -8° to -1° C. Then the reaction liquid was stirred at 0° to -7° C. for 10 minutes, 50.7 g of glycine methyl ester hydrochloride was added at -7° to -4° C. and stirred at -4° to -8° C. for 6 minutes. Next, 40.8 g of triethylamine was added at -8° to -3° 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 1200 g, chloroform-1 to 3% of methanol as the eluent) to obtain 70.5 g of N-[(2-oxo-1-pyrrolidinyl)acetyl]glycine methyl ester as the oily substance. This was dissolved in 120 ml of methanol and 21.7 g of potassium hydroxide dissolved in 150 ml of methanol was added thereto. After reacting at room temperature for 5 hours, 40 g of acetic acid was added. The solvent was distilled off under reduced pressure and the residue was purified through the chromatography on silica gel (silica gel 1 kg, chloroform-5 to 20% of methanol-1% of formic acid as the eluent) and crystallized from tetrahydrofuran to obtain the titled compound.

1. customThen the reaction liquid
2. stirringstirred at -4° to -8° C. for 6 minutes
3. customThe reaction liquid
4. customto room temperature
5. customover 2 hours
6. filtrationtriethylamine hydrochloride was filtered off
7. distillationDimethylformamide was distilled off under reduced pressure
8. customthe residue was purified through the chromatography on silica gel (silica gel 1200 g, chloroform-1 to 3% of methanol as the eluent)

ORD record

ord-a6d31ae8647a42f3aca8e0e8cbe8ee6d

Source dataset

uspto-grants-1989_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04880819