Lithium Hexamethyldisilazide → HCID 66603364, compound
Reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:21])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:32]NS(C1C=CC=CC=1)(=O)=O>C1COCC1>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:14](=[O:21])[CH:15]([F:32])[CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
5
Conditions
- Temperature
- -78 °C
Procedure
To a solution of (4S)-benzyl-3-heptanoyl-oxazolidin-2-one (12.0 g, 41.4 mmol) in THF (30 ml) stirred under N2 at −78° C. was added dropwise a solution of lithium bis(trimethylsilyl)amide (50 ml of 1 M soln. in THF, 50 mmol). This was stirred 1 h at −78° C. then added to solution of N-fluorobenzenesulfonamide (14.3 g, 45.5 mmol) in THF (60 ml) stirred under N2 at −78° C. The reaction mixture was stirred 2.5 h at −78° C. then quenched with aqueous amonium chloride. The product mixture was partitioned between EtOAc and water. The organic extract was washed with brine, dried and all volitiles removed. Chromatography on silica (10% EtOAc 90% hexane) afforded 10.08 g (79%) of the title compound. Mass spectrum ES+: 308 [M+H]+
Workup
- stirringstirred under N2 at −78° C
- stirringThe reaction mixture was stirred 2.5 h at −78° C.
- customthen quenched with aqueous amonium chloride
- customThe product mixture was partitioned between EtOAc and water
- extractionThe organic extract
- washwas washed with brine
- customdried
- customall volitiles removed
Sources & evidence
- ORD record
- ord-b18c357554dd45ac908fab2283f72b39
- Source dataset
- uspto-grants-2007_01
- Patent number
- US07166624B2
Reaction notes
Loading…