Trifluoroacetic acid → HCID 22262083, compound

HRID 1610334Notes

Reaction equation

HRID 1610334 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:28])[CH:9]([NH:20]C(=O)OC(C)(C)C)[CH2:10][C:11]2[O:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[NH2:20][CH:9]([CH2:10][C:11]1[O:12][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:14][CH:15]=1)[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[OH:28]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86593233HCID 86593233, compound

Product 1

HCID 22262083HCID 22262083, compoundYield 101.8%

Procedure

To 1,1-dimethylethyl (1RS,2SR)-2-(4-fluorophenyl)-2-hydroxy-1-((5-(trifluoromethyl)-2-furanyl)methyl)ethylcarbamate (1.70 g, 4.21 mmol) was added trifluoroacetic acid (15 ml) at 0° C. and the mixture was stirred for 10 min. The reaction solution was concentrated, diluted with water (20 ml) and extracted with ethyl acetate (20 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether-hexane to give (1RS,2SR)-2-amino-1-(4-fluorophenyl)-3-(5-(trifluoromethyl)-2-furanyl)-1-propanol (1.30 g, 100%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additiondiluted with water (20 ml)
  3. extractionextracted with ethyl acetate (20 ml×2)
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was recrystallized from diisopropyl ether-hexane

Sources & evidence

ORD record
ord-6ca15213fd6845c190083e88ac5af45a
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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