Methanol → HCID 86707358, compound

HRID 239974Notes

Reaction equation

HRID 239974 reaction equation
[OH-].[Na+].[OH:3][CH2:4][CH:5]1[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]1.CO>O.C1COCC1>[OH:3][CH2:4][CH:5]1[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]1

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86707356HCID 86707356, compound

Product 1

HCID 86707358HCID 86707358, compoundYield 33.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of NaOH (0.16 g) in H2O (1 ml) is added to a stirred solution of methyl 4-[[6-[3-(hydroxymethyl)pyrrolidin-1-yl]-3-methyl-pyridine-2-carbonyl]amino]-3,5-dimethyl-benzoate (0.35 g, 0.88 mmol) in THF:MeOH (5 ml:1 ml). After 8 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 diethyl ether and filtered to afford the title compound as an off-white solid (73 mg, 33.7%). Mass spectrum (m/z): 384.2 (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 diethyl ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-a26c8ad0ebcf47b086bd731a3d689686
Source dataset
uspto-grants-2014_02
Patent number
US08642768B2

Reaction notes

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