Methyl chloroformate → HCID 86655220, compound

Participants

Reaction Steps

A solution of 4-amino-2-(aminomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide (832.5 mg, 2.5 mmol) in pyridine (20 ml) was stirred at room temperature for 30 mins. Methyl chloroformate (708.5 mg, 7.5 mmol) was then added to the mixture and it was stirred at room temperature for overnight. The solution was concentrated in vacuo and the residue was purified by prep. HPLC (column: Luna 300×50.0 mm, 10 u; liquid phase: [A-H2O+0.025% TFA; B-MeCN] B %: 5%-45%, 30 min) to give methyl 5-amino-2-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)benzylcarbamate (208 mg, 21.28%) as a yellow solid and methyl 3-(methoxycarbonylamino)methyl)-4-(N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)sulfamoyl)phenylcarbamate (445 mg, 39.64%) as an orange solid.

Provenance & Evidence