(4S,7S)-4-(3-Bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid [1-(4-methoxy-phenyl)ethyl]-amide → (4R,7S)-4-(3-Bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

HRID 910764ノート

反応式

HRID 910764 の反応式
COC1C=CC(C([NH:11][C:12]([C:14]2[C@@H:23]([C:24]3[CH:29]=[C:28]([O:30][CH2:31][CH3:32])[C:27]([OH:33])=[C:26]([Br:34])[CH:25]=3)[C:22]3[C:21](=[O:35])[CH2:20][C@@H:19]([CH2:36][CH2:37][CH3:38])[CH2:18][C:17]=3[NH:16][C:15]=2[CH3:39])=O)C)=CC=1>C(O)(C(F)(F)F)=O>[Br:34][C:26]1[CH:25]=[C:24]([C@H:23]2[C:22]3[C:21](=[O:35])[CH2:20][C@@H:19]([CH2:36][CH2:37][CH3:38])[CH2:18][C:17]=3[NH:16][C:15]([CH3:39])=[C:14]2[C:12]#[N:11])[CH:29]=[C:28]([O:30][CH2:31][CH3:32])[C:27]=1[OH:33]

参加物

3

反応物 1

HCID 67418207(4S,7S)-4-(3-Bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid [1-(4-methoxy-phenyl)ethyl]-amide

生成物 1

HCID 67417503(4R,7S)-4-(3-Bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carbonitrile

試薬・触媒・溶媒 1

HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
75 °C

実験手順

A solution of (4S,7S)-4-(3-Bromo-5-ethoxy-4-hydroxy-phenyl)-2-methyl-5-oxo-7-propyl-1,4,5,6,7,8-hexahydro-quinoline-3-carboxylic acid [1-(4-methoxy-phenyl)ethyl]-amide (Example 72d, 1.43 g) was dissolved in TFA (30 mL) and stirred at 75° C. for 1 hr. The TFA was evaporated in vacuo and the residue was then dissolved in dichloromethane (30 ml). Triethylamine (1.04 g) and trifluoroacetic acid anhydride (0.95 g) were added dropwise at 0° C. for 15 minutes. The reaction was stirred for 1 hr and the reaction mixture was washed with water (20 ml). The organic layer was dried (MgSO4), filtered, concentrated in vacuo and concentrated. The residue was purified by chromatography on silicagel in heptane/ethyl acetate 1/0->0/1 (v/v) as eluent.

後処理

  1. customThe TFA was evaporated in vacuo
  2. dissolutionthe residue was then dissolved in dichloromethane (30 ml)
  3. additionTriethylamine (1.04 g) and trifluoroacetic acid anhydride (0.95 g) were added dropwise at 0° C. for 15 minutes
  4. stirringThe reaction was stirred for 1 hr
  5. washthe reaction mixture was washed with water (20 ml)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography on silicagel in heptane/ethyl acetate 1/0->0/1 (v/v) as eluent

出典と根拠

ORDレコード
ord-2434d039a48f44dca8d4286666e077d9
出典データセット
uspto-grants-2011_09
特許番号
US08022218B2

反応ノート

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