Triethylamine → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 2,2-difluoroacetic acid (0.0083 mL, 0.131 mmol) in anhydrous dichloromethane (1 mL) at 0° C. under N2 was treated with isobutyl chloroformate (0.014 mL, 0.105 mmol) and triethylamine (0.025 mL). The resulting mixture was stirred at 0° C. for 40 minutes, and the product from Example 200 (50 mg, 0.088 mmol) was added, followed by triethylamine (0.060 mL). The resulting mixture was stirred at room temperature for 90 minutes and partitioned between water and dichloromethane (3×). The combined organic layers were concentrated in vacuo, and the crude product was purified by column chromatography on C18 silica gel using a solvent gradient of 0-100% acetonitrile in water (0.1% trifluoroacetic acid). The title compound was obtained as a trifluoroacetic acid salt (23 mg). 1H NMR (300 MHz, CDCl3) δ ppm 0.89-1.06 (m, 4 H) 1.92-4.89 (m, 14 H) 5.38-5.56 (m, 1 H) 5.70-5.89 (m, 1 H) 7.46-7.76 (m, 4 H) 7.86-8.10 (m, 2 H); MS (ESI) m/z 540 (M+H)+.

Provenance & Evidence