Bromoacetic Acid → HCID 58513728, compound

Participants

Reaction Steps

To an ambient suspension of NaH (5.40 g, 135 mmol) in N,N-dimethylformamide (50 mL) was added dropwise a solution of tert-butyl 3-hydroxy-3-(thiazol-2-yl)pyrrolidine-1-carboxylate (7.30 g, 27 mmol) in N,N-dimethylformamide (20 mL). After 30 minutes, bromoacetic acid (7.50 g, 54.0 mmol) in N,N-dimethylformamide (20 mL) was added dropwise. The solution was stirred at room temperature for 16 hours and then heated to 50° C. for 3 hours. The reaction was cooled to room temperature and was quenched by the addition of water. The solution was basicified to pH 10 by the addition of 2.5 M NaOH solution. The aqueous layer was extracted with ether, and the organics discarded. The aqueous layer was acidified to pH 1 with 6 M HCl solution, and then extracted with ethyl acetate (2×). The combined organics were washed with water, brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the product. MS ESI(+) m/z 329.3 [M+H]+.

Provenance & Evidence