Trifluoroacetic acid → 2-(4-Fluoro-3-methyl-benzyl)-hexanoic acid hydroxyamide

HRID 1158125Notes

Reaction equation

HRID 1158125 reaction equation
O1CCCCC1[O:7][NH:8][C:9](=[O:24])[CH:10]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([CH3:23])[CH:17]=1)[CH2:11][CH2:12][CH2:13][CH3:14].FC(F)(F)C(O)=O>ClCCl>[OH:7][NH:8][C:9](=[O:24])[CH:10]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([CH3:23])[CH:17]=1)[CH2:11][CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 595125952-(4-Fluoro-3-methyl-benzyl)-hexanoic acid (tetrahydro-pyran-2-yloxy)-amide

Product 1

HCID 249913682-(4-Fluoro-3-methyl-benzyl)-hexanoic acid hydroxyamideYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-Fluoro-3-methyl-benzyl)-hexanoic acid (tetrahydro-pyran-2-yloxy)-amide (0.0.358 g, 1.062 mmol) in 5 mL of dichloromethane, was added trifluoroacetic acid (5 mL). After stirring at room temperature for 3 h, the reaction mixture was concentrated under reduced pressure. The product was isolated by Flash chromatography (silica gel) eluting with 0-10% methanol/dichoromethane to give the title compound as an off-white solid (0.059 g, 22% yield). LC-MS: tR=7.1 min; m/z 254 (M+H)+; 1H NMR (300 MHz, CD3OD) δ 0.89 (t, J=6.60 Hz, 3H), 1.27-1.36 (m, 4H), 1.39-1.49 (m, 1H), 1.60-1.67 (m, 1H), 2.23 (d, J=1.50 Hz, 3H), 2.24-2.32 (m, 1H), 2.62 (dd, J=13.50, 5.40 Hz, 1H), 2.79 (dd, J=13.50, 9.60 Hz, 1H), 6.88 (t, J=9.60 Hz, 1H), 6.95-6.96 (m, 1H), 7.01 (t, J=7.50 Hz, 1H).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe product was isolated by Flash chromatography (silica gel)
  3. washeluting with 0-10% methanol/dichoromethane

Sources & evidence

ORD record
ord-ba1228c67a3249d1938958e84f1c5cc1
Source dataset
uspto-grants-2010_10
Patent number
US07807720B2

Reaction notes

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