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

HRID 1487175Notes

Reaction equation

HRID 1487175 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(OC(=O)C)(=O)C>[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

4

Reactant 2

HCID 1176UreaHCID 86699672(S)-2-(1-ethoxy-1-oxopropan-2-yl)malonic acid

Product 1

HCID 86699673(S)-ethyl 2-(2,4,6-trioxohexahydropyrimidin-5-yl)propanoateYield 50%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A suspension of (S)-2-(1-ethoxy-1-oxopropan-2-yl)malonic acid (5 g, 25 mmol) and urea (1.8 g, 29.4 mmol) in acetic anhydride (15 mL) was placed in a microwave reactor and allowed to react under microwave irradiation at 60° C. for 30 minutes. After cooled to room temperature, the mixture was quenched by sodium bicarbonate and extracted with ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, concentrated and purified by silica gel chromatography to afford the product (S)-ethyl 2-(2,4,6-trioxohexahydropyrimidin-5-yl)propanoate (2.85 g, yield 50%).

Workup

  1. customwas placed in a microwave reactor
  2. customto react under microwave irradiation at 60° C. for 30 minutes
  3. customthe mixture was quenched by sodium bicarbonate
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-dbd037c0278742be8cfe74bea9182869
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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