Ammonium Chloride → HCID 67105363, compound
Reaction equation
CON(C)[C:4](=[O:18])[C@@H:5]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:6].C([Mg]Cl)(C)C.[F:25][C:26]1[CH:27]=[C:28]([Mg]Br)[CH:29]=[C:30]([F:32])[CH:31]=1.[NH4+].[Cl-]>C1COCC1.CCOCC>[F:25][C:26]1[CH:27]=[C:28]([C:4](=[O:18])[C@@H:5]([NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH3:6])[CH:29]=[C:30]([F:32])[CH:31]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -15 °C
Procedure
To a −15° C. solution of benzyl {(1S)-2-[methoxy(methyl)amino]-1-methyl-2-oxoethyl}carbamate (1.96 g, 7.36 mmol) in THF (9.4 mL) was added i-propyl magnesium chloride (3.6 mL of a 2M solution in Et2O, 7.2 mmol). The reaction was stirred at −15° C. for 15 minutes and then 3,5-difluorophenylmagnesium bromide (29.44 mL of a 0.5 M solution in THF, 14.72 mmol) was added. The reaction was warmed to room temperature and stirred for 24 hours. The reaction was then poured into saturated NH4Cl (100 mL) and extracted with EtOAc (3×100 mL). The organic extracts were washed with water and brine (100 mL each), dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (15% EtOAc/hexanes) afforded benzyl [(1S)-2-(3,5-difluorophenyl)-1-methyl-2-oxoethyl]carbamate. Rf=0.34 (15% EtOAc/hexanes). LCMS=342.3 (M+Na)+.
Workup
- temperatureThe reaction was warmed to room temperature
- stirringstirred for 24 hours
- extractionextracted with EtOAc (3×100 mL)
- washThe organic extracts were washed with water and brine (100 mL each)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customPurification of the residue by flash chromatography on silica gel (15% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-24fc2732fbcf49dcb8a06916ebe6f533
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07652049B2
Reaction notes
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