Sodium Hydroxide → [5-(3,5-Difluorophenyl)-5-methyl-2,4-dioxo-3-pyridin-2-ylimidazolidin-1-yl]acetic acid

HRID 1685383Notes

Reaction equation

HRID 1685383 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][N:6]1[C:10]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([F:19])[CH:13]=2)([CH3:11])[C:9](=[O:20])[N:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:7]1=[O:27])C.[OH-].[Na+]>C1COCC1.CS(C)=O>[F:18][C:16]1[CH:17]=[C:12]([C:10]2([CH3:11])[N:6]([CH2:5][C:4]([OH:28])=[O:3])[C:7](=[O:27])[N:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[C:9]2=[O:20])[CH:13]=[C:14]([F:19])[CH:15]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 123216751Ethyl[5-(3,5-difluorophenyl)-5-methyl-2,4-dioxo-3-pyridin-2-ylimidazolidin-1-yl]acetate

Product 1

HCID 59370421[5-(3,5-Difluorophenyl)-5-methyl-2,4-dioxo-3-pyridin-2-ylimidazolidin-1-yl]acetic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl[5-(3,5-difluorophenyl)-5-methyl-2,4-dioxo-3-pyridin-2-ylimidazolidin-1-yl]acetate, isomer A from Step A (67.0 mg, 0.172 mmol) in THF (2 mL) was added a solution of 1 N NaOH (0.516 mL, 0.516 mmol) and stirring continued for 16 h. The reaction mixture was diluted with DMSO (1 mL) and purified directly by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. Lyophilization provided the racemic title compound. MS: m/z=362 (M+1).

Workup

  1. custompurified directly by HPLC
  2. washeluting with a gradient of H2O

Sources & evidence

ORD record
ord-eab673f8b7994c44a61afb6d7fbb1931
Source dataset
uspto-grants-2012_04
Patent number
US08148390B2

Reaction notes

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