Trifluoroacetic acid → (S)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)-N-hydroxyhexanamide

HRID 1643274Notes

Reaction equation

HRID 1643274 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([O:25][CH3:26])[CH2:9][C@H:10]([CH2:21][CH2:22][CH2:23][CH3:24])[C:11]([NH:13][O:14]C2CCCCO2)=[O:12])=[CH:4][CH:3]=1.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:25][CH3:26])[CH2:9][C@H:10]([CH2:21][CH2:22][CH2:23][CH3:24])[C:11]([NH:13][OH:14])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59568840(2S)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)-N-(tetrahydro-2H-pyran-2-yloxy)hexanamide

Product 1

HCID 59568803(S)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)-N-hydroxyhexanamideYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S)-2-((R)-2-(4-fluorophenyl)-2-methoxyethyl)-N-(tetrahydro-2H-pyran-2-yloxy)hexanamide (43 mg, 0.12 mmol) in 3 mL DCM was slowly added 3 mL TFA followed by stirring for 30 min at room temperature. The solvent was evaporated and the product isolated by flash column chromatography eluting with 0% to 10% methanol/DCM to give 26 mg of the title compound as white solid.

Workup

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

Sources & evidence

ORD record
ord-4948e05f6fd746e3b5a6432f1295709c
Source dataset
uspto-grants-2012_02
Patent number
US08119692B2

Reaction notes

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