Triethylamine → HCID 669317, compound

Participants

Reaction Conditions

Reaction Steps

Dichloromethane (150 mL) and then triethylamine (33.0 mL, 234 mmol, 2.0 eq.) were added to glycine methyl ester hydrochloride (14.7 g, 117 mmol, 1.0 eq.). The mixture was stirred and cooled to 2° C. using an ice/water bath. A solution of 3,4-dichlorobenzoyl chloride (24.55 g, 117 mmol, 1.0 eq.) in dichloromethane (75 mL) was added over 7 minutes. The mixture was stirred for 1 hour at 2° C., then left to stir at room temperature overnight (16 hours). Water (225 mL) was added and the mixture was stirred rapidly for 30 minutes at room temperature. The layers were separated. The organic layer was washed with water (225 mL), then evaporated to dryness using a rotary evaporator to give an off-white solid. The isolated solid (26.18 g, 85%) was added to dichloromethane (300 mL, 10 vols.) with 1 M sodium hydroxide solution (300 mL, 10 vols). The lower organic layer was concentrated to dryness in vacuo (25.91 g, 84%).

Provenance & Evidence