(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 910764노트

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HRID 910764 반응식
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]

참가 물질

3

반응물 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

생성물 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

시약·촉매·용매 1

HCID 6422Trifluoroacetic acid용매

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온도
75 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2434d039a48f44dca8d4286666e077d9
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022218B2

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