Hexane → HCID 10612452, compound
Reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.CCCCCC.[C:25](Cl)(=[O:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>C1COCC1>[C:25]([N:9]1[C@@H:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:12][O:11][C:10]1=[O:13])(=[O:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 4-(S)-benzyloxazolidin-2-one (56 mmol) (Aldrich, Milwaukee, Wis.) in THF at −78° C. was added 2.5 M n-BuLi in hexane (22.4 mL, 56 mmol) and the reaction stirred at −78° C. for 2 hr. To this was added via cannula a −78° C. solution of hexanoyl chloride (65 mmol) in THF and the mixture stirred at −78° C. for 2 hr, then allowed to warm to room temperature and stirred overnight. The reaction was then quenched with aqueous saturated NH4Cl, extracted with ethyl acetate, dried, and purified by silica gel chromatography (hexanes/ethyl acetate) to afford N-hexanoyl-4-(S)-benzyloxazolidin-2-one.
Workup
- stirringthe mixture stirred at −78° C. for 2 hr
- temperatureto warm to room temperature
- stirringstirred overnight
- customThe reaction was then quenched with aqueous saturated NH4Cl
- extractionextracted with ethyl acetate
- customdried
- custompurified by silica gel chromatography (hexanes/ethyl acetate)
Sources & evidence
- ORD record
- ord-d9164195e61f4e5caa4a23d1271621d5
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06797820B2
Reaction notes
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