Reaction equation
[CH3:1][S:2]([C:5]1[S:6][C:7]([C:10](=O)[CH2:11][CH3:12])=[CH:8][N:9]=1)(=[O:4])=[O:3].[CH3:14][C:15]([S@:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>C1COCC1.C(OCC)C.O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:1][S:2]([C:5]1[S:6][C:7](/[C:10](=[N:20]\[S:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19])/[CH2:11][CH3:12])=[CH:8][N:9]=1)(=[O:4])=[O:3]Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Procedure
A mixture of 1-(2-methanesulfonyl-thiazol-5-yl)-propan-1-one (110 mg, 0.50 mmol), (R)-2-methyl-2-propanesulfinamide (70 mg, 0.6 mmol) and titanium (IV) isopropoxide (0.29 mL, 1.0 mmol) in THF (10 mL) is warmed at reflux. After 18 hours, the mixture is cooled to room temperature and diluted with diethyl ether (100 mL) and water (6 mL). After 10 minutes with stirring, the solution is dried over sodium sulfate, filtered and concentrated. The crude product is purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc in hexanes to afford 2-methyl-propane-2-sulfinic acid [1-(2-methanesulfonyl-thiazol-5-yl)-prop-(Z)-ylidene]-amide.
Workup
- temperatureis warmed
- temperatureat reflux
- dry with materialthe solution is dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product is purified by silica gel chromatography
- washeluting with a gradient of 0-100% EtOAc in hexanes
Sources & evidence
- ORD record
- ord-cd07506f52b145dbb3b0cede6d322b09
- Source dataset
- uspto-grants-2015_01
- Patent number
- US08927550B2
Linked notes
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