Trifluoroacetic acid → HCID 22261434, compound

HRID 1610451Notes

Reaction equation

HRID 1610451 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([OH:29])[CH:9]([NH:21]C(=O)OC(C)(C)C)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[NH2:21][CH:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=1)[CH:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([Cl:1])[N:7]=1)[OH:29]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 91393564HCID 91393564, compound

Product 1

HCID 22261434HCID 22261434, compoundYield 79%

Procedure

To 1,1-dimethylethyl(1RS,2RS)-2-(6-chloro-2-pyridyl)-2-hydroxy-1-((4-(trifluoromethyl)phenyl)methyl)ethylcarbamate (500 mg, 1.16 mmol) was added trifluoroacetic acid (8 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,2RS)-2-amino-1-(6-chloro-2-pyridyl)-3-(4-(trifluoromethyl)phenyl)-1-propanol (302 mg, 79%).

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-80ed573153324a64af9f186a9404e9e0
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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