1-Hydroxybenzotriazole → HCID 21904700, compound

Participants

Reaction Steps

N-N-Diisopropylethylamine (44 μL, 0.25 mmol), HOBt (20 mg, 0.15 mmol) and WSCDI (23 mg, 0.12 mmol) were added to the acid from step (i) (35 mg, 0.10 mmol) in CH2Cl2 (2 mL) and stirred for 30 min. (NH4)2CO3 (19 mg, 0.20 mmol) was added and the mixture was stirred at room temperature for 16 h. The reaction mixture was partitioned between water (10 mL) and CH2Cl2 (10 mL) and the organic layer was dried (MgSO4) and evaporated. The residue was purified by column chromatography [SiO2; DCM/MeOH/880 NH3 (93:7:1)] and then triturated with Et2O to give the desired product (20 mg, 57%) as a white solid; δH (CDCl3, 400 MHz) 2.35 (6H, s), 3.62 (2H, s), 5.66 (1H, br), 6.00 (1H, br), 7.18 (2H, m), 7.26 (2H, m), 8.23 (1H, d), 8.50 (1H, d); MS m/z (TS+) 356 (MH+).

Provenance & Evidence