Water → HCID 23075278, compound

Participants

Reaction Conditions

Reaction Steps

Methyl 3-(2,2-difluoro-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)acetamido)benzoate 19 (0.50 g, 1.20 mmol) was dissolved in methanol (33.5 mL). Water (3.35 mL) was added via syringe at RT and KOH (0.27 g, 4.81 mmol) was added. The reaction mixture was heated at 70° C. for 2 h. After cooling to RT the mixture was evaporated in vacuo. The crude product was dissolved in water (30 mL) and extracted with ether (2×50 mL). The aqueous layer was acidified by a solution of HCl 1M to about pH=1. The aqueous layer was extracted with ether (2×100 mL), dried over MgSO4, filtered and evaporated. The crude product was purified by column chromatography using as eluent cyclohexane: EtOAc=98:02. 3-(2,2-Difluoro-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)acetamido)benzoic acid 20 was obtained (0.41 g, 84% yield) as an orange solid.

Provenance & Evidence