Triethylamine → HCID 23075283, compound

Participants

Reaction Conditions

Reaction Steps

Difluoro-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetic acid 16 (306 mg, 1.08 mmol) was dissolved in SOCl2 and two drops of DMF were added at 0° C. The mixture was stirred at 0° C. for 30 min then evaporated and the product was dissolved in CH2Cl2 (7 mL). B) Methyl 4-(aminomethyl)benzoate SLA 07006 (179 mg, 1.08 mmol) and DMAP (14 mg, 0.11 mmol) were dissolved in CH2Cl2 (7 mL) and Et3N (1.5 mL) at 0° C. A) was added at 0° C. via syringe in B) and the resulting mixture was stirred at 0° C. for 10 min and abandoned at RT for 1 h. Aqueous NH4Cl 5% (100 mL) was added and the mixture extracted with EtOAc (3×50 mL). The organic layer was washed with NaHCO3 5% (3×100 mL) and brine (3×100 mL), dried over MgSO4, filtered and evaporated in vacuo. The crude product was purified by flash chromatography using as eluent cyclohexane:EtOAc=9:1. Methyl 4-((2,2-difluoro-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)acetamido)methyl)-benzoate 21 was obtained (0.27 g, 58% yield) as a beige solid.

Provenance & Evidence