Triethylamine → HCID 66681229, compound

Participants

Reaction Steps

Under ice-cooling, 1.73 mL (12.4 mmol) of triethylamine and 0.88 mL (7.23 mmol) of 2,2-dimethyl propanoyl chloride were added to a THF (10 mL) solution comprising 1.50 g (6.97 mmol) of 1-(tert-butoxycarbonyl)-L-proline, and the mixture was stirred under ice-cooling for 30 minutes. Subsequently, 269 mg (4.65 mmol) of methyl 2-amino-5-chlorobenzoate was added thereto under ice-cooling, and the mixture was heated under reflux for 19 hours. After condensation and addition of water, the mixture was extracted with ethyl acetate. The organic layer was washed with 0.1% hydrochloric acid, water, saturated sodium bicarbonate water, and saturated saline, followed by drying over magnesium sulfate. After condensation, the resultant was purified by silica gel column chromatography (n-hexane/ethyl acetate=10/1→4/1), thereby giving 1.65 g of tert-butyl (2S)-2-{[4-chloro-2-(methoxycarbonyl)phenyl]carbamoyl}pyrrolidine-1-carboxylate (yield: 93%).

Provenance & Evidence