2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 59556922, compound

HRID 1967327Notes

Reaction equation

HRID 1967327 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([C:21]([OH:23])=O)[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[N:20])=[CH:15][CH:14]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH3:24][C:25]1(C)OC(=O)CC(=O)[O:26]1.S([O-])(O)(=O)=O.[K+]>CN(C1C=CN=CC=1)C.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:10]2[C:25](=[O:26])[CH:24]=[C:21]([OH:23])[CH:11]2[CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[CH:17][CH:18]=2)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

6

Reactant 3

HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 516920Potassium bisulfateHCID 67105481HCID 67105481, compound

Product 1

HCID 59556922HCID 59556922, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3-chloro-4-cyanophenyl)-4-cyanophenylalanine (1.57 g), Meldrum's acid (0.76 g) and 4-(N,N-dimethylamino)pyridine (0.88 g) in tetrahydrofuran (70 mL) was added N,N′-carbonyldiimidazole (0.94 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 organic layer was washed with water and saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was washed with ethyl acetate-isopropyl ether to give the title compound as pale-yellow crystals (yield: 578 mg, 34%).

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. washthe organic layer was washed with water and saturated brine
  9. dry with materialdried over magnesium sulfate
  10. customThe solvent was evaporated under reduced pressure
  11. washthe obtained residue was washed with ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-79b68b30590146f8bbe108fc515f7681
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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