Acetic Acid → tert-butyl (6SR,7SR)-6-amino-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

Temperature

2.5 °C

To a solution of cobalt bromide (15 mg) in ethanol (5 mL) was added 2,2′-bipyridyl (33 mg), sodium tetrahydroborate (53 mg) was added, and the mixture was stirred at 0-5° C. for 5 min. To the reaction mixture was added a solution of tert-butyl (6SR,7SR)-6-azido-7-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (270 mg) in ethanol (5 mL), and the mixture was stirred at 0-5° C. for 30 min. Acetic acid was added to the reaction mixture, and the mixture was stirred at room temperature for 5 min. The solvent was evaporated under reduced pressure. The residue was neutralized with saturated aqueous sodium hydrogen carbonate, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (191 mg).

1. additionwas added
2. stirringthe mixture was stirred at 0-5° C. for 30 min
3. stirringthe mixture was stirred at room temperature for 5 min
4. customThe solvent was evaporated under reduced pressure
5. extractionthe mixture was extracted with ethyl acetate
6. washThe extract was washed with brine
7. dry with materialdried over anhydrous sodium sulfate
8. customThe solvent was evaporated under reduced pressure
9. customThe residue was purified by silica gel column chromatography

ORD record

ord-1253be1d357643009d53a3f1f5bbcd89

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722662B2