Bromoacetic Acid → HCID 68584488, compound

Participants

Reaction Conditions

Reaction Steps

Compound 25B (2.17 g, 13.2 mmol) in 40 mL of dichloromethane was treated with a premixed solution of 1,3-dicyclohexylcarbodiimide (3 g, 14.5 mmol) and bromoacetic acid (1.84 mg, 13.2 mmol) in 30 mL of dichloromethane. The reaction was stirred for 1 hour and then quenched with 50 mL of water and extracted with dichloromethane (3×50 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and excess solvent removed via rotary evaporator. The crude product was then dissolved in 30 mL of DMSO and potassium carbonate (2.27 g, 16.5 mmol) was added to the mixture. The reaction was heated to 60° C. overnight then cooled and poured oven ice water. The resulting precipitate was collected be filtration to give 200 mg (7%) of desired product. MS (electrospray): mass calculated for C12H16N2O, 204.13; m/z found 205.1, [M+H]+.

Provenance & Evidence