Triethylamine → HCID 18409288, compound

Participants

Reaction Steps

To a solution of 2-phenoxybenzoic acid (Aldrich Chemical Co.) (111 mg, 0.518 mmol) and DMF (2 drops) in CH2Cl2 (1.5 mL) was added oxalyl chloride (389 μL, 2.0M in CH2Cl2, 0.777 mmol). The reaction bubbled for 10 min, then was stirred at RT under argon for 1.5 h. The reaction was concentrated in vacuo, and the resulting residue was dissolved in CH2Cl2 (1.5 mL) and added dropwise to a solution of Example 204 Part A compound (172 mg, 0.432 mmol) and triethylamine (90 μL, 0.648 mmol) in CH2Cl2 (1.5 mL) at 0° C. under argon. The reaction was stirred at 0° C. for 10 min, diluted with CH2Cl2 (20 mL), washed with saturated NaHCO3 (5 mL) and brine (5 mL), then dried over Na2SO4. Evaporation gave a yellow oil, which was dissolved in a minimum amount of CH2Cl2 and purified by flash chromatography on silica gel (50 g) eluting with 30% EtOAc/hexane to provide title compound (211 mg, 82%) as a yellow gum.

Provenance & Evidence