Trifluoroacetic acid → (R)-4-(4-fluoro-3-methylphenyl)-N-hydroxy-4-methoxybutanamide

HRID 1643266Notes

Reaction equation

HRID 1643266 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:21][CH3:22])[CH2:9][CH2:10][C:11]([NH:13][O:14]C2CCCCO2)=[O:12])=[CH:4][C:3]=1[CH3:23].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([O:21][CH3:22])[CH2:9][CH2:10][C:11]([NH:13][OH:14])=[O:12])=[CH:4][C:3]=1[CH3:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 723283874-(4-fluoro-3-methylphenyl)-4-methoxy-N-(tetrahydro-2H-pyran-2-yloxy)butanamide

Product 1

HCID 59568787(R)-4-(4-fluoro-3-methylphenyl)-N-hydroxy-4-methoxybutanamideYield 66.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To the solution of 4R)-4-(4-fluoro-3-methylphenyl)-4-methoxy-N-(tetrahydro-2H-pyran-2-yloxy)butanamide (66 mg, 0.2 mmol) in 4 mL DCM was slowly added 2 mL TFA and the resulting solution stirred for 30 min at 25° C. The solvent was evaporated and the product isolated by flash column chromatography eluting with 0% to 10% methanol/DCM gradient solvent to give 32 mg of the title compound as a white solid.

Workup

  1. customThe solvent was evaporated
  2. customthe product isolated by flash column chromatography
  3. washeluting with 0% to 10% methanol/DCM gradient solvent

Sources & evidence

ORD record
ord-502338ffe17f4039a7e9dcdefbb287df
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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