Sulfuric Acid → HCID 53651351, compound

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)

1. extractionthe mixture was extracted with EtOAc and dichloromethane (100 mL each)
2. dry with materialThe combined organics were dried over sodium sulfate
3. concentrationconcentrated
4. additionDMF (5 mL) was added
5. extractionextracted with EtOAc
6. dry with materialThe organic layer was dried over sodium sulfate
7. concentrationconcentrated

ORD record

ord-90945e8859d84e5a9f926b3f987835ac

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265434B1