Succinic anhydride → [1-(4-Cyano-3-trifluoromethylphenyl)-2,5-dioxo-3-methyl-4-phenylimidazolidin-4-yl]methoxy-4-oxobutanoic acid

HRID 389901Notes

Reaction equation

HRID 389901 reaction equation
[CH3:1][N:2]1[C:6]([CH2:13][OH:14])([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:5](=[O:15])[N:4]([C:16]2[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:17]=2)[C:3]1=[O:28].CN(C1C=CC=CN=1)C.[C:38]1(=[O:44])[O:43][C:41](=[O:42])[CH2:40][CH2:39]1>N1C=CC=CC=1>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([N:4]2[C:5](=[O:15])[C:6]([CH2:13][O:14][CH:40]([CH2:39][CH:38]=[O:44])[C:41]([OH:43])=[O:42])([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:2]([CH3:1])[C:3]2=[O:28])=[CH:17][C:18]=1[C:24]([F:25])([F:27])[F:26])#[N:21]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 218852-DimethylaminopyridineHCID 59317181HCID 59317181, compound

Product 1

HCID 86641463[1-(4-Cyano-3-trifluoromethylphenyl)-2,5-dioxo-3-methyl-4-phenylimidazolidin-4-yl]methoxy-4-oxobutanoic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 0.20 g of 4-[3-methyl-4-hydroxymethyl-2,5-dioxo-4-phenylimidazolidin-1-yl]-2-trifluoromethylbenzonitrile in 3 mL of pyridine was added 6 mg of dimethylaminopyridine and 0.052 g of succinic anhydride. The mixture is stirred for 12 hours then evaporated to dryness. The crude product is washed with water and extracted with DCM. The organic layer is dried over magnesium sulfate, filtered and evaporated. The crude product is purified by chromatography over silica gel while eluting with 50/50 cyclohexane/ethyl acetate to give the desired compound.

Workup

  1. customthen evaporated to dryness
  2. washThe crude product is washed with water
  3. extractionextracted with DCM
  4. dry with materialThe organic layer is dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product is purified by chromatography over silica gel
  8. washwhile eluting with 50/50 cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-fed29da682984e2ca983f7301bf2f139
Source dataset
uspto-grants-2013_02
Patent number
US08383608B2

Reaction notes

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