Isobutyl chloroformate → HCID 67311500, compound

Participants

Reaction Steps

To a solution of 4-amino-2-(aminomethyl)-N-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-6-yl)benzenesulfonamide (500 mg, 0.89 mmol) and TEA (360 mg, 3.6 mmol) in THF (200 mL) at −20° C. was slowly added iso-butyl chloroformate (121 mg, 0.89 mmol) in THF (10 mL). Then the mixture was stirred at room temperature for 2 hrs. The mixture 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 %: 15%-40%, 25 min) to give the title compound (185 mg, 38%) as TFA salt. 1H NMR DMSO 400 MHz δ 9.98 (s, 1H), 7.52 (d, J=8.8 Hz, 1H), 7.43 (q, 2H), 7.20 (d, J=8.8 Hz, 1H), 7.11 (q, 1H), 6.48 (s, 1H), 6.35 (q, 1H), 4.84 (s, 2H), 4.50 (s, 2H), 3.75 (d, J=7.2 Hz, 2H), 1.84 (q, 1H), 0.88 (q, 6H).

Provenance & Evidence