Methanol → HCID 86707347, compound

HRID 239963Notes

Reaction equation

HRID 239963 reaction equation
[OH-].[Na+].[OH:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[N:16]=[C:15]([C:17]([NH:19][C:20]3[C:29]([CH3:30])=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][C:21]=3[CH3:31])=[O:18])[C:14]([CH3:32])=[CH:13][CH:12]=2)[CH2:6]1.CO>C1COCC1>[OH:3][CH2:4][CH:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]2[N:16]=[C:15]([C:17]([NH:19][C:20]3[C:21]([CH3:31])=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:28][C:29]=3[CH3:30])=[O:18])[C:14]([CH3:32])=[CH:13][CH:12]=2)[CH2:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86707345HCID 86707345, compound

Product 1

HCID 86707347HCID 86707347, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of aqueous 2N NaOH (2.00 ml) is added to a stirred solution of methyl 4-(6-(3-(hydroxymethyl)piperidin-1-yl)-3-methylpicolinamido)-3,5-dimethylbenzoate (0.06 g, 0.146 mmol) in THF:MeOH (4 ml:1 ml). After 12 hours at ambient temperature, the organic solvent is removed under reduced pressure and the residue is diluted with water, acidified to pH 3 with aqueous citric acid solution, and extracted with ethyl acetate (2×10 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 filtered to afford the title compound as an off-white solid (0.03 g, 48%). Mass spectrum (m/z): 398.2 (M+1).

Workup

  1. customthe organic solvent is removed under reduced pressure
  2. additionthe residue is diluted with water
  3. extractionextracted with ethyl acetate (2×10 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
  7. filtrationfiltered

Sources & evidence

ORD record
ord-c8fb47a043c446968936deba654c70b9
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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