反応式
C(Cl)(=O)C(Cl)=O.[F:7][C:8]1[CH:9]=[C:10]([CH:15]([CH2:31][CH2:32][OH:33])[CH2:16][N:17]([CH3:30])[C:18]([C:20]2[C:29]3[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=3[CH:23]=[CH:22][CH:21]=2)=[O:19])[CH:11]=[CH:12][C:13]=1[F:14].C(N(CC)CC)C.O>C(Cl)Cl.CS(C)=O>[F:7][C:8]1[CH:9]=[C:10]([CH:15]([CH2:31][CH:32]=[O:33])[CH2:16][N:17]([CH3:30])[C:18]([C:20]2[C:29]3[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=3[CH:23]=[CH:22][CH:21]=2)=[O:19])[CH:11]=[CH:12][C:13]=1[F:14]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 2
反応条件
- 温度
- -78 °C
実験手順
To a stirred cooled (−78° C.) solution of oxalyl chloride (0.546 mL, 6.26 mmol) in DCM (2.55 mL) was added DMSO (0.888 mL, 12.52 mmol) in DCM (3.94). The solution was stirred at −78° C. for 5 min and a solution of N-[2-(3,4-difluorophenyl)-4-hydroxybutyl]-N-methyl-5,6,7,8-tetrahydro-1-naphthamide (1.17 g, 3.13 mmol) in DCM (6.3 mL) and DMSO (3.32 mL) was added dropwise. The solution was stirred at −78° C. for 15 min and triethylamine (2.52 mL, 18.1 mmol) was added. Stirring was continued at −78° C. for 30 min and then at room temperature for 2 h. Additional H2O and DCM (25 mL) were added, the layers separated, and the organic layer was dried (MgSO4), filtered, and concentrated in vacuo. Purification by chromatography (silica gel; Et2O) provided the title compound (1.10 g, 95%) as a brown gum. MS m/z 372 (M+H).
後処理
- stirringThe solution was stirred at −78° C. for 15 min
- stirringStirring
- waitwas continued at −78° C. for 30 min
- waitat room temperature for 2 h
- customthe layers separated
- dry with materialthe organic layer was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customPurification by chromatography (silica gel; Et2O)
出典と根拠
- ORDレコード
- ord-633c904b8b6343848bcf19521287a5f8
- 出典データセット
- uspto-grants-2002_06
- 特許番号
- US06403601B1
関連ノート
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