Triethylamine → HCID 53961439, compound

Participants

Reaction Steps

To a solution of (+/-)-3-(3-cyclopentyloxy-4-methoxyphenyl)-3-phenylethynylpropionic acid (0.50 g, 1.37 mmol) and dimethyl formamide (3 drops) in dichloromethane (10 mL) at room temperature under an argon atmosphere was dropwise added oxalyl chloride (0.125 mL, 1.44 mmol). The reaction was stirred 0.5 h, was evaporated, was dissolved in tetrahydrofuran (5 mL) and was added to a solution of 1-amino-2-butanol (0.15 mL, 1.52 mmol) and triethylamine (0.23 mL, 1.64 mmol) in tetrahydrofuran (10 mL) and was stirred at room temperature under an argon atmosphere for 1 h. Water was added, the reaction was extracted with three times dichloromethane, was dried (MgSO4) and was evaporated. Purification by flash chromatography, eluted with 2:98 methanol:dichloromethane provided the title compound (0.54 g, 91%) as a white solid, mp.94-96° C.

Provenance & Evidence