Potassium Bromide → HCID 11535949, compound
Reaction equation
[C:1]([N:8]([CH3:16])[C@H:9]([CH2:14][OH:15])[C@H:10]([CH2:12][CH3:13])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])(O)=O.[Na+].[K+].[Br-].Cl[O-].[Na+]>ClCCl.O>[C:4]([O:3][C:1](=[O:2])[N:8]([C@H:9]([CH:14]=[O:15])[C@@H:10]([CH3:11])[CH2:12][CH3:13])[CH3:16])([CH3:5])([CH3:7])[CH3:6]Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 37.0 g Boc-N-methyl-isoleucinol (160 mmol) in 160 ml dichloromethane was added a solution of 5.4 g NaHCO3 (64 mmol) and 1.9 g KBr (16 mmol) in 160 ml deionized water. The reaction mixture was cooled to 0° C. and after the addition of 125 mg 2,2,6,6-tetramethyl-piperidin-1-oxyl (TEMPO, 0.8 mmol), 122.6 g 10.2% aqueous sodium hypochlorite (176 mmol Cl2) were added under stirring over 2.5 h at 0-5°. After additional stirring for 30 min the excess of NaOCl was destroyed by the addition of ca. 1 ml 38% aqueous sodium bisulfite and the reaction mixture was warmed up to 20°. The aqueous layer was extracted with 160 ml dichloromethane and the organic layers were washed with 10% brine and dried (Na2SO4). Removal of the solvent by rotary evaporation afforded 35.7 g (97.2%) crude product as a light orange oil.
Workup
- additionwere added
- customwas destroyed by the addition of ca. 1 ml 38% aqueous sodium bisulfite
- temperaturethe reaction mixture was warmed up to 20°
- extractionThe aqueous layer was extracted with 160 ml dichloromethane
- washthe organic layers were washed with 10% brine
- dry with materialdried (Na2SO4)
- customRemoval of the solvent
- customby rotary evaporation
Sources & evidence
- ORD record
- ord-80e796c49084484dba863498ed90ed37
- Source dataset
- uspto-grants-2007_12
- Patent number
- US07312343B2
Reaction notes
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