Urea → (R)-ethyl 2-(2,4,6-trioxohexahydropyrimidin-5-yl)propanoate

HRID 1487182Notes

Reaction equation

HRID 1487182 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C@@H:5]([CH:7]([C:11]([OH:13])=O)[C:8]([OH:10])=O)[CH3:6])[CH3:2].[NH2:15][C:16]([NH2:18])=[O:17].C([O-])(O)=O.[Na+]>CC(OC(C)=O)=O>[O:17]=[C:16]1[NH:18][C:8](=[O:10])[CH:7]([C@@H:5]([CH3:6])[C:4]([O:3][CH2:1][CH3:2])=[O:14])[C:11](=[O:13])[NH:15]1

Participants

5

Reactant 3

HCID 1176UreaHCID 516892Sodium BicarbonateHCID 86699678(R)-2-(1-ethoxy-1-oxopropan-2-yl)malonic acid

Product 1

HCID 86699679(R)-ethyl 2-(2,4,6-trioxohexahydropyrimidin-5-yl)propanoate

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

The (R)-2-(1-ethoxy-1-oxopropan-2-yl)malonic acid (3.5 g, 0.017 mol) and the urea (1.03 g, 0.017 mol) was dissolved into Ac2O (20 ml) and then added to the reaction vessel of the microwave reactor and were allowed to react under microwave irradiation at 60° C. for half an hour. After cooled to rt, added NaHCO3 aqueous and extracted with EtOAc. The organic phase was dried and concentrated to afford (R)-ethyl 2-(2,4,6-trioxohexahydropyrimidin-5-yl)propanoate, which was purified by silica gel chromatography (2.0 g, 52%).

Workup

  1. additionadded to the reaction vessel of the microwave reactor
  2. customto react under microwave irradiation at 60° C. for half an hour
  3. extractionextracted with EtOAc
  4. customThe organic phase was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-705be88de5a5457a8a4e029f732e6a1e
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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