Iodoethane → [5-(3,5-Difluorophenyl)-5-methyl-2,4-dioxo-3-ethylimidazolidin-1-yl]acetic acid

HRID 1685381Notes

Reaction equation

HRID 1685381 reaction equation
C([O:3][C:4](=[O:22])[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])[NH:8][C:7]1=[O:21])C.C(=O)([O-])[O-].[K+].[K+].I[CH2:30][CH3:31].[OH-].[Na+]>CN(C=O)C.CS(C)=O>[F:19][C:14]1[CH:13]=[C:12]([C:10]2([CH3:11])[N:6]([CH2:5][C:4]([OH:3])=[O:22])[C:7](=[O:21])[N:8]([CH2:30][CH3:31])[C:9]2=[O:20])[CH:17]=[C:16]([F:18])[CH:15]=1

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 91574597Ethyl[5-(3,5-difluorophenyl)-5-methyl-2,4-dioxoimidazolidin-1-yl]acetate

Product 1

HCID 59370420[5-(3,5-Difluorophenyl)-5-methyl-2,4-dioxo-3-ethylimidazolidin-1-yl]acetic acid

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl[5-(3,5-difluorophenyl)-5-methyl-2,4-dioxoimidazolidin-1-yl]acetate, isomer A from Step D (50.0 mg, 0.160 mmol) in DMF (1 mL) was added potassium carbonate (33.0 mg, 0.192 mmol) and iodoethane (0.015 mL, 0.192 mmol). The reaction was stirred at ambient temperature for 18 h and then a solution of 1 N NaOH (0.480 mL, 0.480 mmol) was added and stirring continued for 3 h. The reaction mixture was diluted with DMSO (1 mL), filtered, 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=313 (M+1).

Workup

  1. stirringstirring
  2. waitcontinued for 3 h
  3. filtrationfiltered
  4. custompurified directly by HPLC
  5. washeluting with a gradient of H2O

Sources & evidence

ORD record
ord-430c9e3db6d344d5a8e06db62361d47e
Source dataset
uspto-grants-2012_04
Patent number
US08148390B2

Reaction notes

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