Trifluoroacetic acid → HCID 178436204, compound
Reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[CH:10]([C:12]1[N:13]=[CH:14][N:15](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:16]=1)O)[CH3:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl.O1CCCC1.C(OCC)(=O)C>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[CH2:10][C:12]1[N:13]=[CH:14][NH:15][CH:16]=1)[CH3:2]Participants
Procedure
This compound was prepared using methodology described in J. Chem. Soc., Perkin Trans. 1, 2002, 1061-1066. To a stirred solution of 0.35 g (0.76 mmol) rac-(2-ethyl-6-methyl-phenyl)-(1-trityl-1H-imidazol-4-yl)-methanol in 5 ml dichloromethane were added dropwise 1.22 ml (7.63 mmol) triethylsilane and 0.69 ml (9.16 mmol) trifluoroacetic acid. The reaction mixture was stirred at room temperature for 16 hours, and then diluted with a 1:1 mixture of tetrahydrofuran and ethyl acetate. The mixture was washed sequentially with 2 N aqueous sodium hydroxide solution and saturated brine and then the organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, methanol/dichloromethane gradient) to afford 40 mg (26%) of the title compound as a yellow crystalline solid. MS (ISP): 201.3 ([M+H]+).
Workup
- customThis compound was prepared
- washThe mixture was washed sequentially with 2 N aqueous sodium hydroxide solution and saturated brine
- dry with materialthe organic phase was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by flash chromatography (silica gel, methanol/dichloromethane gradient)
Sources & evidence
- ORD record
- ord-2c621c276f23414d82894b5e663b0340
- Source dataset
- uspto-grants-2012_04
- Patent number
- US08158668B2
Reaction notes
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