Triethylamine → HCID 23075289, 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 (0.53 g, 1.88 mmol) was dissolved in SOCl2 and two drops of DMF were added at 0° C. The mixture was stirred at 0° C. for 0.5 h, evaporated and the crude product was dissolved in CH2Cl2 (5 mL). B) Methyl-3-aminobenzoate (284 mg, 1.88 mmol) and DMAP (23 mg, 0.19 mmol) were dissolved in CH2Cl2 (5 mL) and Et3N (2.6 mL) was added at 0° C. A) was added in B) at 0° C. and this mixture was stirred at 0° C. for 10 min and abandoned at RT for 1 h. The mixture was poured in aqueous NH4Cl 5% (100 mL) and extracted with EtOAc (3×50 mL). The organic layer was washed with NaHCO3 (2×100 mL), brine (2×100 mL), dried with MgSO4, filtered and evaporated. The crude product was purified by column chromatography using as eluent cyclohexane:EtOAc=90:10.Methyl 3-(2,2-difluoro-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)acetamido)benzoate 19 was obtained (0.55 g, 70% yield) as a yellow oil.

Provenance & Evidence