Dimethylcarbamoyl Chloride → Ethyl 2-(4-chloro-6-(dimethylcarbamoyloxy)-1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Participants

Reaction Steps

To a solution of ethyl 2-(4-chloro-1,6-dihydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (60 mg, 0.22 mmol) in DMF (3 mL) was slowly added NaH (27 mg, 0.66 mmol) at 0° C. The mixture was stirred for 20 min and N,N-dimethylcarbamic chloride (29 mg, 0.27 mmol) was added at 0° C. The reaction mixture was stirred overnight at room temperature and quenched with ice water. The resulting mixture was extracted with EtOAc (2×15 mL) and the combined extracts were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was used directly in the next step reaction without further purification. MS (ESI) m/z=342 [M+H]+.

Provenance & Evidence