Methanol → HCID 86707361, compound

HRID 239977Notes

Reaction equation

HRID 239977 reaction equation
[OH-].[Li+].[F:3][C:4]1([F:32])[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[C:14]([C:16]([NH:18][C:19]3[C:28]([CH3:29])=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][C:20]=3[CH3:30])=[O:17])[C:13]([CH3:31])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1.O.CO>C1COCC1>[F:32][C:4]1([F:3])[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[C:14]([C:16]([NH:18][C:19]3[C:20]([CH3:30])=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:27][C:28]=3[CH3:29])=[O:17])[C:13]([CH3:31])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 86707362HCID 86707362, compound

Product 1

HCID 86707361HCID 86707361, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (LiOH.H2O, 0.048 g, 0.00115 mol) is added to a stirred solution of methyl 4-[[6-(4,4-difluoro-1-piperidyl)-3-methyl-pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoate (0.24 g, 0.575 mmol) in THF:H2O:MeOH (1.5 ml:0.7 ml:1.5 ml). After 3 hours at 50° C., the organic solvent is removed under reduced pressure and the residue is diluted with water, acidified to pH 6 with aqueous 1N HCl, and extracted with ethyl acetate (3×20 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 diethyl ether and filtered to afford the title compound as a white solid (0.166 g, 71%). Mass spectrum (m/z): 404.2 (M+1).

Workup

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

Sources & evidence

ORD record
ord-e2f205dd09834aaca5d1c5323dab9312
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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