Methanol → 4-[[5-(4-Hydroxy-1-piperidyl)-2-(trifluoromethyl)benzoyl]amino]-3,5-dimethyl-benzoic acid

HRID 1427146Notes

Reaction equation

HRID 1427146 reaction equation
[OH-].[Na+].[Si]([O:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:18]=[CH:19][C:20]([C:38]([F:41])([F:40])[F:39])=[C:21]([CH:37]=2)[C:22]([NH:24][C:25]2[C:34]([CH3:35])=[CH:33][C:28]([C:29]([O:31]C)=[O:30])=[CH:27][C:26]=2[CH3:36])=[O:23])[CH2:13][CH2:12]1)(C(C)(C)C)(C)C.CO>C1COCC1>[OH:10][CH:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:18]=[CH:19][C:20]([C:38]([F:41])([F:39])[F:40])=[C:21]([CH:37]=2)[C:22]([NH:24][C:25]2[C:26]([CH3:36])=[CH:27][C:28]([C:29]([OH:31])=[O:30])=[CH:33][C:34]=2[CH3:35])=[O:23])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86707379Methyl 4-[[5-[4-[tert-butyl(dimethyl)silyl]oxy-1-piperidyl]-2-(trifluoromethyl)benzoyl]amino]-3,5-dimethyl-benzoate

Product 1

HCID 867073814-[[5-(4-Hydroxy-1-piperidyl)-2-(trifluoromethyl)benzoyl]amino]-3,5-dimethyl-benzoic acidYield 68.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of aqueous 2N NaOH (1.5.00 ml) is added to a stirred solution of methyl 4-[[5-[4-[tert-butyl(dimethyl)silyl]oxy-1-piperidyl]-2-(trifluoromethyl)benzoyl]amino]-3,5-dimethyl-benzoate (60.0 mg, 133.20 μmoles) in THF:MeOH (5 ml:0.5 ml). After 12 h at ambient temperature, the organic solvent is removed under reduced pressure and the residue is diluted with water, acidified to pH4 with aqueous citric acid, and extracted with ethyl acetate (2×20 ml). The organic layers are combined and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure and the resulting precipitate is triturated with pentane and diethyl ether filtered to afford the title compound as an off-white solid (0.04 g, 60%). Mass spectrum (m/z): 437.2 (M+1).

Workup

  1. customthe organic solvent is removed under reduced pressure
  2. additionthe residue is diluted with water
  3. extractionextracted with ethyl acetate (2×20 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe resulting precipitate is triturated with pentane and diethyl ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-a29b46824aa5453890e8b8923f944b76
Source dataset
uspto-grants-2015_01
Patent number
US08933098B2

Reaction notes

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