Tetrahydrofuran → (S)-N-[4-(trifluoromethyl)phenyl]-3-methanesulfonyloxypentanoic acid amide

HRID 1354538Notes

Reaction equation

HRID 1354538 reaction equation
O1CCCC1.[CH3:6][S:7](Cl)(=[O:9])=[O:8].[F:11][C:12]([F:28])([F:27])[C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:26])[CH2:21][C@@H:22]([OH:25])[CH2:23][CH3:24])=[CH:15][CH:14]=1.C(N(CC)CC)C>C(OCC)(=O)C.O>[F:11][C:12]([F:27])([F:28])[C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:26])[CH2:21][C@@H:22]([O:25][S:7]([CH3:6])(=[O:9])=[O:8])[CH2:23][CH3:24])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11961982(S)-N-[4-(trifluoromethyl)phenyl]-3-hydroxypentanoic acid amide

Product 1

HCID 11961983(S)-N-[4-(trifluoromethyl)phenyl]-3-methanesulfonyloxypentanoic acid amide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A tetrahydrofuran solution (2 mL) containing 703 mg (6.14 mmol) of methanesulfonyl chloride was added dropwise to a tetrahydrofuran solution (8 mL) containing 1.07 g (4.09 mmol) of (S)-N-[4-(trifluoromethyl)phenyl]-3-hydroxypentanoic acid amide produced in Example 2 and 621 mg (6.14 mmol) of triethylamine at 0° C. for 10 minutes. After stirring at the same temperature for lhour, water (25 mL) and ethyl acetate (30 mL) were added to carry out extraction. The organic layer was washed with saturated brine, and dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure to obtain (S)-N-[4-(trifluoromethyl)phenyl]-3-methanesulfonyloxypentanoic acid amide as a yellow solid (1.48 g, crude yield: 97%). 1H-NMR (CDCl3, 400 MHz/ppm): δ 1.04 (3H, t), 1.91 (2H, m), 2.73-2.87 (2H, m), 3.15 (3H, s), 5.01-5.09 (1H, m), 7.56 (2H, d), 7.66 (2H, d), 7.83 (1H, br)

Workup

  1. additionwere added
  2. extractionextraction
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-242b2ddb7a7447dda407a3cc2283ca6c
Source dataset
uspto-grants-2007_05
Patent number
US07223859B2

Reaction notes

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