Trifluoroacetic acid → HCID 69670816, compound

HRID 1191653Notes

Reaction equation

HRID 1191653 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[CH2:16][CH:17]([OH:22])[C:18]([CH3:21])([CH3:20])[CH3:19])(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[CH2:16][CH:17]([OH:22])[C:18]([CH3:20])([CH3:19])[CH3:21]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67684799Tert-butyl[4-methoxy-2-(2-hydroxy-3,3-dimethylbutyl)phenyl]carbamate

Product 1

HCID 69670816HCID 69670816, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl[4-methoxy-2-(2-hydroxy-3,3-dimethylbutyl)phenyl]carbamate (234 mg) in dichloromethane (2 mL) was added trifluoroacetic acid (1 mL) at room temperature, and the mixture was stirred for one hour. The reaction mixture was poured into 5% aqueous sodium hydrogen carbonate solution (40 mL) and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the title compound (157 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3888dfb0daf2490b94e35d7b963ee660
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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