Ammonium Chloride → HCID 71294185, compound
Reaction equation
Br[C:2]1[S:3][C:4]([CH:7]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[C:8]([F:11])([F:10])[F:9])=[CH:5][N:6]=1.C([Li])CCC.CON(C)[C:28](=[O:30])[CH3:29].[Cl-].[NH4+]>C1COCC1.O>[Si:13]([O:12][CH:7]([C:4]1[S:3][C:2]([C:28](=[O:30])[CH3:29])=[N:6][CH:5]=1)[C:8]([F:11])([F:10])[F:9])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]Participants
Conditions
- Temperature
- -78 °C
Procedure
In THF (5 mL) was dissolved 2-bromo-5-(1-(tert-butyldimethylsilyloxy)-2,2,2-trifluoroethyl)thiazole (515 mg, 1.37 mmol) obtained in Step 2. n-Butyllithium (1.65 mol/L solution in n-hexane, 1.24 mL, 2.05 mmol) was added dropwise at −78° C. and the mixture was stirred at −78° C. for 30 minutes. A solution of N-methoxy-N-methylacetamide (1.38 mL, 13.7 mmol) in THF (1 mL) was added to the reaction mixture and the mixture was stirred at −78° C. for 2 hours. A saturated aqueous ammonium chloride solution and water were added to the reaction mixture. Extraction with ethyl acetate and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give 1-(5-(1-(tert-butyldimethylsilyloxy)-2,2,2-trifluoroethyl) thiazol-2-yl)ethanone (437 mg, 94%).
Workup
- stirringthe mixture was stirred at −78° C. for 2 hours
- extractionExtraction with ethyl acetate
- dry with materialdrying over anhydrous magnesium sulfate
- filtrationAfter filtration
- customthe solvent in the filtrate was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)
Sources & evidence
- ORD record
- ord-fc022655a51a4d51ab9fdb3d421c4ce0
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150569B2
Reaction notes
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