Trifluoroacetic acid → HCID 178519989, compound

HRID 1162321Notes

Reaction equation

HRID 1162321 reaction equation
C(OC(=O)[N:7]([CH:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:26][CH2:25]1)[CH2:8][C:9]1[N:10]=[C:11]([CH2:22][OH:23])[N:12](COCC[Si](C)(C)C)[CH:13]=1)(C)(C)C.C(O)(C(F)(F)F)=O.C(=O)([O-])O.[Na+]>O>[CH2:30]([N:27]1[CH2:28][CH2:29][CH:24]([NH:7][CH2:8][C:9]2[N:10]=[C:11]([CH2:22][OH:23])[NH:12][CH:13]=2)[CH2:25][CH2:26]1)[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 66853665HCID 66853665, compound

Product 1

HCID 178519989HCID 178519989, compoundYield 103.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

tert-Butyl(1-benzyl-4-piperidinyl)((2-(hydroxymethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-4-yl)methyl)carbamate (0.48 g) obtained in Example 83e) was dissolved in a mixed solution (TFA:water=1:1, 2 ml), and mixed at 80° C. for 3 hours. After cooling to room temperature, the mixture was neutralized with a saturated aqueous sodium hydrogen carbonate solution and extracted with chloroform. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure to obtain the title compound as a yellow oil (0.28 g, quantitative).

Workup

  1. additionmixed at 80° C. for 3 hours
  2. extractionextracted with chloroform
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-c1853fcdbb9e43c6a8545c7d339d87fc
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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