1-Hydroxybenzotriazole → HCID 59393690, compound

Participants

Reaction Steps

Compound 1a (350 mg, 0.896 mmol) was added to a stirred solution of acetoxyacetic acid (126 mg, 1.07 mmol), 1[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (205 mg, 1.07 mmol) and 1-hydroxybenzotriazole (157 mg, 1.16 mmol) in DCM (8.00 mL) at rt. After approximately 1 h, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted with EtOAc. The combined organic extracts were washed with water and brine, dried (sodium sulfate) and concentrated in vacuo to afford the title compound 1b, which was used without further purification in the subsequent reaction. m/z (ES) 491 (MH)+ 1HNMR (500 MHz, CDCl3): δ 8.90 (s, 1H), 8.51 (s, 1H), 8.29 (s, 1H), 7.92 (d, 1H, J=8.5 Hz), 7.83 (s, 1H), 7.54 (d, 2H, J=8.0 Hz), 7.50 (d, 2H, J=8.0 Hz), 7.35 (d, 1H, J=8.3 Hz), 5.21 (br, 2H), 4.90 (s, 2H), 4.03 (s, 3H), 3.17 (m, 1H), 2.22 (s, 3H), 1.76 (s, 3H), 0.88 (d, 3H, J=6.4 Hz), 0.84 (d, 3H, J=6.6 Hz).

Provenance & Evidence