Lithium Hydroxide → HCID 11328167, compound

HRID 910325Notes

Reaction equation

HRID 910325 reaction equation
[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N:23]([CH3:34])[C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:25])[CH:18]=2)=[CH:15][CH:16]=1)[C:5]([O:7]CC)=[O:6])[CH3:2].[OH-].[Li+]>O1CCCC1>[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:12]=[N:13][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N:23]([CH3:34])[C:24]([NH:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[O:25])[CH:18]=2)=[CH:15][CH:16]=1)[C:5]([OH:7])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67147864HCID 67147864, compound

Product 1

HCID 11328167HCID 11328167, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60 mg (0.13 mmol) of ethyl 2-ethoxy-3-{6-[3-(3-heptyl-1-methylureido)phenyl]pyrid-3-yl}propanoate are placed in 4 ml of tetrahydrofuran, 0.2 ml (0.2 mmol) of aqueous 1M lithium hydroxide solution is added and the mixture is stirred at room temperature for 24 hours. After acidic hydrolysis to pH 4.5-5, the reaction medium is extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated. The residue obtained is purified by thin-layer chromatography on silica eluted with a 50/50 heptane/ethyl acetate mixture and then a 90/10 dichloromethane/methanol mixture. 40 mg (70%) of 2-ethoxy-3-{6-[3-(3-heptyl-1-methylureido)phenyl]pyrid-3-yl}propanoic acid are obtained in the form of a white solid with a melting point of 142-143° C.

Workup

  1. customAfter acidic hydrolysis to pH 4.5-5
  2. extractionthe reaction medium is extracted with ethyl acetate
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by thin-layer chromatography on silica
  8. washeluted with a 50/50 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-3e23f29b3be54a9585887c472d559dc5
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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