2,2-Dimethyl-1,3-dioxane-4,6-dione → HCID 59557014, compound

HRID 1173649Notes

Reaction equation

HRID 1173649 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([C:15]([OH:17])=O)[CH2:12][CH2:13][CH3:14])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[CH3:18][C:19]1(C)OC(=O)CC(=O)[O:20]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:19](=[O:20])[CH:18]=[C:15]([OH:17])[CH:11]2[CH2:12][CH2:13][CH3:14])[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 67105491HCID 67105491, compound

Product 1

HCID 59557014HCID 59557014, compoundYield 43.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(3-chloro-4-cyanophenyl)norvaline (4.0 g), Meldrum's acid (2.40 g) and 4-(N,N-dimethyl)aminopyridine. (2.90 g) in tetrahydrofuran (60 mL) was added N,N′-carbonyldiimidazole (3.08 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 (60 mL), and the mixture was refluxed for 45 min. After allowing to room temperature, the mixture was extracted twice 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 washed with ethyl acetate to give the title compound as colorless crystals (yield: 1.89 g, 43%).

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 (60 mL)
  6. temperaturethe mixture was refluxed for 45 min
  7. customAfter allowing to room temperature
  8. extractionthe mixture was extracted twice 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. washthe obtained residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-a4396fb8b2d74e67a4d8cc9b9b8bd614
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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