HCID 90933529, compound → HCID 22261947, compound

HRID 1610511Notes

Reaction equation

HRID 1610511 reaction equation
[F:1][C:2]1[N:7]=[C:6]([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]([O:17][C:18]([F:23])([F:22])[CH:19]([F:21])[F:20])[CH:12]=2)[CH:5]=[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]([O:17][C:18]([F:22])([F:23])[CH:19]([F:20])[F:21])[CH:12]=1)[CH:8]([C:6]1[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=1)[OH:32]

Participants

3

Reactant 1

HCID 90933529HCID 90933529, compound

Product 1

HCID 22261947HCID 22261947, compoundYield 103.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 1,1-dimethylethyl(1RS,2RS)-2-(6-fluoropyridin-2-yl)-2-hydroxy-1-((3-(1,1,2,2-tetrafluoroethoxy)phenyl)methyl)ethylcarbamate (1.6 g, 3.46 mmol) was added trifluoroacetic acid (20 ml), and the mixture was stirred at room temperature for 10 min. The reaction solution was concentrated under reduced pressure, and 1N aqueous sodium hydroxide solution (10 ml) was added. The mixture was extracted with ethyl acetate (20 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure to give (1RS,2RS)-2-amino-1-(6-fluoropyridin-2-yl)-3-(3-(1,1,2,2-tetrafluoroethoxy)phenyl)-1-propanol (1.3 g, 100%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure, and 1N aqueous sodium hydroxide solution (10 ml)
  2. additionwas added
  3. extractionThe mixture was extracted 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

Sources & evidence

ORD record
ord-05236abe3b9c4668a3c43108c15c9ce3
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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