Reaction equation
[CH3:1][C@H:2]1[C@@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4](=[O:13])[N:3]1[C:14](=[O:19])[CH2:15][CH2:16][CH2:17][CH3:18].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].FC(F)(F)S(O[CH2:36][CH3:37])(=O)=O>C1COCC1>[CH2:36]([C@@H:15]([CH2:16][CH2:17][CH3:18])[C:14]([N:3]1[C@@H:2]([CH3:1])[C@@H:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[O:5][C:4]1=[O:13])=[O:19])[CH3:37]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a −78° C. stirred solution of the (4S,5R)-4-Methyl-3-pentanoyl-5-phenyl-oxazolidin-2-one (9.20 g, 35.2 mmol) in dry THF (150 mL) was added NaHMDS (42.2 mL, 1.0 M in THF) dropwise. After 1 hour, ethyl trifluoromethanesulfonate (5.93 mL, 45.7 mmol) was added dropwise and the reaction was stirred at −78° C. for an additional 2 hours. The reaction was warmed to −30° C. for 30 minutes and quenched with sat. NH4Cl. The layers were separated and the aqueous layer was extracted with EtOAc (3×40 mL). The organic extracts were combined and washed with brine (2×40 mL). The organic phase was dried over MgSO4, filtered, and concentrated under reduced pressure to yield 8.05 g of crude product.
Workup
- temperatureThe reaction was warmed to −30° C. for 30 minutes
- customquenched with sat. NH4Cl
- customThe layers were separated
- extractionthe aqueous layer was extracted with EtOAc (3×40 mL)
- washwashed with brine (2×40 mL)
- dry with materialThe organic phase was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-bbdfddf93c574bb091dc437a8140f82e
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07179934B2
Linked notes
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