Water → HCID 11774368, compound

Participants

Reaction Conditions

Reaction Steps

4-[2,2-Difluoro-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetylamino]-benzoic acid 18 (170 mg, 0.425 mmol) was dissolved in SOCl2 (2.4 mL) and two drops of DMF were added at 0° C. The mixture was stirred at 0° C. for 1 h and evaporated and the crude product was dissolved in CH2Cl2 (5 mL). B) Hydroxylamine hydrochloride (1.38 g, 20 mmol) was dissolved in THF (17.2 mL) and water (3.45 mL) and Et3N (3.45 mL) at 0° C., the mixture was stirred at 0° C. for 1 h. A was added in B at 0° C. and this mixture was stirred at 0° C. for 10 min and at RT for 17.75 h. The mixture was evaporated and water was added (50 ml) before to be extracted with CH2Cl2 (3×50 mL). The organic layer was washed with brine (2×20 mL) and dried with MgSO4, filtered and evaporated. The crude product was purified by column chromatography using as eluent cyclohexane:AcOEt=99:1. 4-(2,2-Difluoro-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-7-yl)acetamido)-N-hydroxybenzamide EHT 9299 was obtained (58.3 mg, 33.4% yield) as a pink solid.

Provenance & Evidence