Trifluoroacetic acid → HCID 22262354, compound

HRID 1610639Notes

Reaction equation

HRID 1610639 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:32])[CH:9]([NH:24]C(=O)OC(C)(C)C)[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18])[CH:12]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[NH2:24][CH:9]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([C:20]([F:22])([F:23])[F:21])(=[O:19])=[O:18])[CH:12]=1)[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[OH:32]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86593284HCID 86593284, compound

Product 1

HCID 22262354HCID 22262354, compound

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-{3-[(trifluoromethyl)sulfonyl]benzyl}-ethylcarbamate (620 mg, 1.30 mmol) was added trifluoroacetic acid (5 ml), and mixture was stirred at 0° C. for 10 min. After the reaction solution was concentrated, saturated aqueous sodium hydrogen carbonate was added and the mixture was extracted with ethyl acetate (30 ml×2). The extract was washed with saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure to give the objective substance (0.52 g, 100%).

Workup

  1. concentrationAfter the reaction solution was concentrated
  2. additionsaturated aqueous sodium hydrogen carbonate was added
  3. extractionthe mixture was extracted with ethyl acetate (30 ml×2)
  4. washThe extract was washed with saturated brine
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. customevaporated under reduced pressure
  7. customto give the objective substance (0.52 g, 100%)

Sources & evidence

ORD record
ord-42f0ee0524954316a8d5ce33805cc41b
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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