Sulfuric Acid → (2R)-5,5,5-Trifluoro-2-hydroxypentanoic acid

Temperature

0 °C

To a cool (0° C.), stirred solution of (2R)-2-amino-5,5,5-trifluoropentanoic acid (4.09 g, 23.90 mmol), prepared according to the process disclosed in U.S. Publication No. 2009/0111858 A1, and H2SO4 (2.8 mL, 52.5 mmol) in water (95 mL) was added a solution of sodium nitrite (9.89 g, 143 mmol) in water (30 mL) dropwise via addition funnel over 60 min. The reaction mixture was allowed to slowly warm to room temperature and stirred overnight. The reaction mixture was diluted with Et2O, the aqueous phase was separated and extracted with Et2O (3×). The combined organics were dried (Na2SO4), filtered and concentrated under reduced pressure to provide Preparation 6B (4.1551 g, >99%) as an amber oil. 1H NMR (400 MHz, CDCl3) δ 4.33 (1H, dd, J=8.03, 4.27 Hz), 2.09-2.42 (3H, m), 1.88-2.02 (1H, m).

1. customprepared
2. additiondropwise via addition funnel over 60 min
3. temperatureto slowly warm to room temperature
4. customthe aqueous phase was separated
5. extractionextracted with Et2O (3×)
6. dry with materialThe combined organics were dried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure
9. customto provide

ORD record

ord-11c29d89785c4150ac432095e7978533

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133126B2