Acetone → HCID 24704998, compound

HRID 883537Notes

Reaction equation

HRID 883537 reaction equation
[C:1](Cl)(=[O:10])[C:2]1[NH:9][C:7](=[O:8])[NH:6][C:4](=[O:5])[CH:3]=1.[NH2:12][C@H:13]([C:17]([OH:19])=[O:18])[CH:14]([CH3:16])[CH3:15].C(=O)=O.CC(C)=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[O:8]=[C:7]1[NH:9][C:2]([C:1]([NH:12][CH:13]([CH:14]([CH3:16])[CH3:15])[C:17]([OH:19])=[O:18])=[O:10])=[CH:3][C:4](=[O:5])[NH:6]1

Participants

7

Reactant 4

HCID 180AcetoneHCID 280Carbon DioxideHCID 6287L-ValineHCID 204910432,6-Dioxo-1,2,3,6-tetrahydropyrimidine-4-carbonyl chloride4×

Product 1

HCID 24704998HCID 24704998, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In a dry 3-necked, round bottomed flask, equipped with a magnetic stirrer, a thermometer, a nitrogen inlet tube and the dropping funnel containing the orotoyl chloride solution, 6.56 g (56 mmol) of Valine is suspended, with stirring, in 50 mL of dry DCM. To this suspension a catalytic amount (˜0.1 mmol) of DMAP is also added. The suspension is stirred in a dry ice and acetone bath to a temperature of about −15° C. When the target temperature is reached the drop wise addition of orotoyl chloride is commenced. Addition of orotoyl chloride continues, with constant cooling and stirring, until all of the orotoyl chloride is added, after which the reaction is allowed to warm to room temperature with constant agitation. The solution is then filtered to remove any remaining Valine and the volatile DCM is removed from the filtrate under reduced pressure, the remainder is then purified by flash chromatography (ethyl acetate/hexanes; 1/6), yielding 2-(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxamido)-3-methylbutanoic acid.

Workup

  1. customIn a dry 3-necked, round bottomed flask, equipped with a magnetic stirrer
  2. temperaturewith constant cooling
  3. filtrationThe solution is then filtered
  4. customto remove any remaining Valine
  5. customthe volatile DCM is removed from the filtrate under reduced pressure
  6. customthe remainder is then purified by flash chromatography (ethyl acetate/hexanes; 1/6)

Sources & evidence

ORD record
ord-2e6648e5405d4aa09259fb95ae9eaa2c
Source dataset
uspto-grants-2012_08
Patent number
US08236952B2

Reaction notes

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