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 2422486Notes

Reaction equation

HRID 2422486 reaction equation
[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

Participants

4

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-508fa60047774ab1b278cdce5fef6e29
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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