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

HRID 1354538ノート

反応式

HRID 1354538 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-242b2ddb7a7447dda407a3cc2283ca6c
出典データセット
uspto-grants-2007_05
特許番号
US07223859B2

反応ノート

読み込み中…