Triethylamine → HCID 59608432, compound

Participants

Reaction Steps

A solution of 5-{[(3-chlorophenyl)methyl]oxy}-2-fluorobenzoic acid (343 mg, 1.22 mmol) in dichloromethane (5 ml) was treated with oxalyl chloride (1.5 eqs, 160 ul, 1.83 mmol) and DMF (1 drop). Effervescence was observed and the mixture was stirred at room temperature for 1 hour. The solvent was then evaporated in vacuo and azeotroped with toluene. A portion of the resulting solid (122 mgs, 0.41 mmol) was dissolved in dichloromethane (5 ml) and treated with triethylamine (2.5 eqs, 142 ul, 1.02 mmol) and methyl 4-(aminomethyl)benzoate hydrochloride (1.5 eqs, 124 mg, 0.61 mmol). The mixture was stirred at room temperature for 18 hours. The mixture was then diluted with methanol and purified by SCX cartridge eluting with methanol. Fractions combined and evaporated to give the title compound as a white solid (227 mg). MS (ES+) m/z 428 [M+H]+ (C23H1935ClFNO4).

Provenance & Evidence