2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 59557022, compound

HRID 1967319Notes

Reaction equation

HRID 1967319 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([C:19]([OH:21])=O)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH3:22][C:23]1(C)OC(=O)CC(=O)[O:24]1.S([O-])(O)(=O)=O.[K+]>CN(C1C=CN=CC=1)C.O1CCCC1>[CH2:12]([CH:11]1[C:19]([OH:21])=[CH:22][C:23](=[O:24])[N:10]1[C:4]1[CH:5]=[CH:6][C:7]([C:8]#[N:9])=[C:2]([Cl:1])[CH:3]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 516920Potassium bisulfateHCID 67105773HCID 67105773, compound

Product 1

HCID 59557022HCID 59557022, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3-chloro-4-cyanophenyl)phenylalanine (2.0 g), Meldrum's acid (1.05 g) and 4-(N,N-dimethylamino)pyridine (1.22 g) in tetrahydrofuran (30 mL) was added N,N′-carbonyldiimidazole (1.29 g) at 0° C., and the mixture was stirred at room temperature overnight. A 5% aqueous potassium hydrogen sulfate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with 5% aqueous potassium hydrogen sulfate solution and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (30 mL), and the mixture was refluxed for 45 min. After allowing to room temperature, the mixture was extracted 3 times with saturated aqueous sodium hydrogen carbonate solution. The aqueous layers were combined, and acidified with citric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was recrystallized from tetrahydrofuran-hexane to give the title compound as pale-yellow crystals (yield: 1.41 g, 65%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 5% aqueous potassium hydrogen sulfate solution and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in ethyl acetate (30 mL)
  6. temperaturethe mixture was refluxed for 45 min
  7. customAfter allowing to room temperature
  8. extractionthe mixture was extracted 3 times with saturated aqueous sodium hydrogen carbonate solution
  9. extractionthe mixture was extracted with ethyl acetate
  10. washThe organic layer was washed with saturated brine
  11. dry with materialdried over magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. customthe obtained residue was recrystallized from tetrahydrofuran-hexane

Sources & evidence

ORD record
ord-8c096587bc0e441ba054c811ac6f72e2
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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