Isopropyl chloroformate → HCID 67173673, 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-propyl chloroformate (97.5 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: Gemini 300×50.0 mm, 10 u; liquid phase: [A-H2O+0.04% NH3OH; B-MeCN] B %: 10%-35%, 25 min) to give the title compound (230 mg, 43%). 1H NMR DMSO 400 MHz δ 9.17 (s, 1H), 7.53 (d, J=8.4 Hz, 1H), 7.44 (d, J=2.0 Hz, 1H), 7.33 (q, 1H), 7.20 (d, J=8.4 Hz, 1H), 7.12 (q, 1H), 6.47 (s, 1H), 6.36 (q, 1H), 6.00 (s, 2H), 4.85 (s, 2H), 4.77 (q, 1H), 4.50 (s, 2H), 1.19 (d, J=6.0 Hz, 6H).

Provenance & Evidence