Triethylamine → HCID 23075285, compound

Participants

Reaction Conditions

Reaction Steps

2,2-Difluoro-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)acetic acid 16 (0.70 g, 2.48 mmol) was dissolved in SOCl2 and two drops of DMF were added at 0° C. This mixture was stirred at 0° C. for 30 min and evaporated in vacuo. The resulting acid chloride was dissolved in CH2Cl2 (5 mL). Methyl-4-aminobenzoate (0.38 g, 2.48 mmol) and DMAP (30 mg, 0.25 mmol) were dissolved in CH2Cl2 (5 mL) and Et3N (2.9 mL) was added at 0° C. The solution of the acid chloride in CH2Cl2 was added and this mixture stirred for 10 min at 0° C. and then abandoned to RT for 1 h. A solution of aqueous NH4Cl 5% was added (200 mL) and the mixture was extracted with EtOAc (3×100 mL). The organic layer was washed with aqueous NaHCO3 5% (2×20 mL), brine (2×20 mL), dried over MgSO4, filtered and evaporated in vacuo. The crude product was purified by chromatography on silica using as eluent cyclohexane:EtOAc=9:1. After evaporation, methyl 4-(2,2-difluoro-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)acetamido)benzoate 17 (0.67 g, 65% yield) was obtained as a beige solid.

Provenance & Evidence