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

HRID 1354538Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1354538
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

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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)

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-242b2ddb7a7447dda407a3cc2283ca6c
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07223859B2

Notizen zur Reaktion

Wird geladen…