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

HRID 1354538노트

반응식

HRID 1354538 반응식
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

참가 물질

7

반응물 4

HCID 8028Tetrahydrofuran2회HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11961982(S)-N-[4-(trifluoromethyl)phenyl]-3-hydroxypentanoic acid amide

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-242b2ddb7a7447dda407a3cc2283ca6c
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07223859B2

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