Water → (S)-2-(1-{[2-chloro-4-(4-fluorophenyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1,1,1-trifluorobutan-2-ol

HRID 2422553Notes

Reaction equation

HRID 2422553 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][C:38]([F:41])=[CH:37][CH:36]=5)=[CH:29][C:30]([Cl:34])=[N: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.[Li+].[OH-].O>C1COCC1>[Cl:34][C:30]1[CH:29]=[C:28]([C:35]2[CH:40]=[CH:39][C:38]([F:41])=[CH:37][CH:36]=2)[C:27]2[C:32](=[CH:33][C:24]([CH2:23][N:21]3[CH:22]=[C:18]([C@@:11]([OH:10])([CH2:12][CH3:13])[C:14]([F:17])([F:15])[F:16])[N:19]=[N:20]3)=[CH:25][CH:26]=2)[N:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 866219831-(1-{[2-chloro-4-(4-fluorophenyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate

Product 1

HCID 86621982(S)-2-(1-{[2-chloro-4-(4-fluorophenyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1,1,1-trifluorobutan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(1-{[2-chloro-4-(4-fluorophenyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1-(trifluoromethyl)propyl 4-nitrobenzoate (300 mg, 0.49 mmol) and LiOH 2M/H2O (1.25 mL, 2.5 mmol) in THF (5 mL) was stirred at rt 5 h. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduce pressure. Purification on silica gel (eluting with acetone/dichloromethane, 1:9) gave the title compound. MS (+ESI): 465 (M+H)+.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification on silica gel (eluting with acetone/dichloromethane, 1:9)

Sources & evidence

ORD record
ord-2d768931b4b644bbbea58c7f6393ecf4
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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