Hydroxylamine → HCID 9879575, compound

Participants

Reaction Conditions

Reaction Steps

In a 50 mL round-bottomed flask was added methyl 2-(N-benzylsulfamoyl)benzoate 43 (49 mg, 0.160 mmol) in THF (321 μl) and MeOH (321 μl) and the solution was cooled to 0° C. Then, a 50% aqueous solution of hydroxylamine (530 mg, 8.02 mmol) was added, followed by a 4M aqueous solution of KOH (80 μl, 0.321 mmol) and the resulting colorless solution was stirred at 0° C., allowing to slowly warm to rt and stirred for 18 h. The reaction mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc and combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide a colorless oil. A solid was obtained by successive dissolution in Et2O/Hex mixture and concentration which was triturated in Et2O to afford title compound 44 (18 mgs, 37% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 11.25 (s, 1H), 9.34 (s, 1H), 7.83 (dd, J=7.6, 1.2 Hz, 1H), 7.67 (td, J=7.4, 1.4 Hz, 1H), 7.61 (td, J=7.6, 1.6 Hz, 1H), 7.50 (dd, J=7.4, 1.6 Hz, 1H), 7.49 (bs, 1H), 7.27-7.18 (m, 5H), 4.05 (d, J=5.9 Hz, 2H). LRMS (ESI): (calc.) 306.34 (found) 307.14 (MH)+

Provenance & Evidence