Water → tert-butyl (4R)-4-{[(benzyloxy)carbonyl]amino}pentanoate

Temperature

80 °C

To a solution of tert-butyl(4S)-4-{[(benzyloxy)carbonyl]amino}-5-bromopentanoate (4.5 g, 11.7 mmol) and tributyltin hydride (6.3 ml, 23.4 mmol) in toluene (45 ml) was added 2,2′-azobisisobutyronitrile (0.19 g, 1.2 mmol) and the mixture was stirred at 80° C. for 20 minutes. To the reaction mixture was added water, and the solution was extracted three times with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and the organic solvent was removed under reduced pressure. The residue was purified with silica gel chromatography to give tert-butyl (4R)-4-{[(benzyloxy)carbonyl]amino}pentanoate (3.5 g, 98%).

1. extractionthe solution was extracted three times with ethyl acetate
2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
3. dry with materialdried over anhydrous sodium sulfate
4. customthe organic solvent was removed under reduced pressure
5. customThe residue was purified with silica gel chromatography

ORD record

ord-bf3169adf428459bac42baf028eefd8b

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07163936B2