Sulfuric Acid → HCID 53651351, compound

Participants

Reaction Steps

A suspension of 2-amino-4,4,4-trifluorobutyric acid (1.1 g, 7 mmol), in 5 mL water was cooled to 0 C. 2N sulfuric acid (3.9 mL, 7.7 mmol) was added followed by 2N sodium nitrite (3.9 mL, 7.7 mmol). After 3 h the mixture was warmed to room temperature and stiffed overnight. Water was added and the mixture was extracted with EtOAc and dichloromethane (100 mL each). The combined organics were dried over sodium sulfate and concentrated. DMF (5 mL) was added followed by triethylamine (1.5 ml, 10.5 mmol) and benzyl bromide (1.25 mL, 10.5 mmol). The resulting mixture was stirred overnight. The mixture was diluted with water and extracted with EtOAc. The organic layer was dried over sodium sulfate and concentrated. Flash chromatography (3/1 Hexane/EtOAc) afforded 438 mg (25 %) of desired product. 1H NMR (400 MHz, CDCl3). δ 2.4-2.55 (m, 1H), 2.63-2.77 (m, 1H), 4.5-4.55 (m, 1H), 5.26 (dd, 2H), 7.35-7.41 (m, 5H)

Provenance & Evidence