Lithium Hydroxide → 2-({[4-(2-{Ethyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethyl)phenyl]thio}methyl)benzoic acid

HRID 899897Notes

Reaction equation

HRID 899897 reaction equation
[CH2:1]([N:3]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=1)[C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:13][C:14]2[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=2[C:16]([O:18]C)=[O:17])=[CH:8][CH:7]=1)[CH3:2].[OH-].[Li+]>C1COCC1.O>[CH2:1]([N:3]([CH2:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]([F:34])([F:33])[F:35])=[CH:30][CH:31]=1)[C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:13][C:14]2[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=2[C:16]([OH:18])=[O:17])=[CH:8][CH:7]=1)[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 69120484Methyl 2-({[4-(2-{ethyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethyl)phenyl]thio}methyl)benzoate

Product 1

HCID 98054702-({[4-(2-{Ethyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethyl)phenyl]thio}methyl)benzoic acidYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-({[4-(2-{ethyl[4-(trifluoromethyl)benzyl]amino}-2-oxoethyl)phenyl]thio}methyl)benzoate (640 mg, 1.276 mmol) was dissolved in THF (20 ml). Lithium hydroxide (61 mg, 2.552 mmol) in water (10 ml) was added. The mixture was stirred at room temperature and the reaction was followed by LC-MS. After 24 hours, more lithium hydroxide (30 mg) and water (10 ml) were added. After in total 70 hour, LC-MS showed the reaction was complete. The mixture was evaporated to remove THF. The residue was washed with diethyl ether, then acidified with 10% HCl, pH=2, and extracted with EtOAc (×2). The extracts were combined and washed with brine, dried with magnesium sulphate and evaporated. Chromatography of the residue on a column (ISOLUTE SI, 5 g/25 ml), using DCM and then MeOH/DCM (0.5:99.5, then 1:99) as eluant, gave the title compound (510 mg), yield 82%.

Workup

  1. waitAfter in total 70 hour
  2. customThe mixture was evaporated
  3. customto remove THF
  4. washThe residue was washed with diethyl ether
  5. extractionextracted with EtOAc (×2)
  6. washwashed with brine
  7. dry with materialdried with magnesium sulphate
  8. customevaporated

Sources & evidence

ORD record
ord-8c8929b45e0e481bbfe6254848a4f26b
Source dataset
uspto-grants-2008_04
Patent number
US07355069B2

Reaction notes

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