Lithium Hydroxide → (S)-4-(3-fluorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)-2H-chromen-2-one

HRID 2422486노트

반응식

HRID 2422486 반응식
[N+](C1C=CC(C([O:10][C@@:11]([C:18]2[N:19]=[N:20][N:21]([CH2:23][C:24]3[CH:33]=[C:32]4[C:27]([C:28]([C:35]5[CH:40]=[CH:39][CH:38]=[C:37]([F:41])[CH:36]=5)=[CH:29][C:30](=[O:34])[O:31]4)=[CH:26][CH:25]=3)[CH:22]=2)([C:14]([F:17])([F:16])[F:15])[CH2:12][CH3:13])=O)=CC=1)([O-])=O.[OH-].[Li+]>C1COCC1>[F:41][C:37]1[CH:36]=[C:35]([C:28]2[C:27]3[C:32](=[CH:33][C:24]([CH2:23][N:21]4[CH:22]=[C:18]([C@:11]([OH:10])([C:14]([F:16])([F:17])[F:15])[CH2:12][CH3:13])[N:19]=[N:20]4)=[CH:25][CH:26]=3)[O:31][C:30](=[O:34])[CH:29]=2)[CH:40]=[CH:39][CH:38]=1

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 86621965(S)-1-(1-{[4-(3-fluorophenyl)-2-oxo-2H-chromen-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

생성물 1

HCID 59774889(S)-4-(3-fluorophenyl)-7-({4-[1-hydroxy-1-(trifluoromethyl)propyl]-1H-1,2,3-triazol-1-yl}methyl)-2H-chromen-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (S)-1-(1-{[4-(3-fluorophenyl)-2-oxo-2H-chromen-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate (15 mg, 0.025 mmol) in THF (2 mL), lithium hydroxide (0.125 mL of 1M solution, 0.125 mmol) was added. After 45 minutes stirring at room temperature, the reaction was quenched by the addition of 0.150 mL of a 2N HCl solution. The mixture was stirred 3 h at room temp and then heated 2 h at 40° C. After cooling, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over MgSO4, filtered and concentrated. The crude residue obtained was purified by column chromatography to afford the title compound. 1H NMR (400 MHz, acetone-d6): 8.21 (s, 1H), 7.7-7.6 (m, 1H), 7.53 (d, 1H), 7.42-7.3 (m, 5H), 6.41 (s, 1H), 5.87 (s, 2H), 5.48 (s, 1H), 2.4-2.3 (m, 1H), 2.1-2.0 (m, 1H), 0.87 (t, 3H).

후처리

  1. customthe reaction was quenched by the addition of 0.150 mL of a 2N HCl solution
  2. stirringThe mixture was stirred 3 h at room temp
  3. temperatureheated 2 h at 40° C
  4. temperatureAfter cooling
  5. additionthe reaction mixture was diluted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude residue obtained
  11. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-508fa60047774ab1b278cdce5fef6e29
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960409B2

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