Potassium Carbonate → HCID 66523188, compound

HRID 1753108Notes

Reaction equation

HRID 1753108 reaction equation
[CH:1]1([C:4](=[O:18])[CH:5]([NH:12][C:13](=O)[CH2:14][O:15][CH3:16])[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.O=P(Cl)(Cl)Cl.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:1]1([C:4]2[O:18][C:13]([CH2:14][O:15][CH3:16])=[N:12][C:5]=2[CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 90093577HCID 90093577, compound

Product 1

HCID 66523188HCID 66523188, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 4-Cyclopropyl-3-[(methoxyacetyl)amino]-4-oxobutanoate (Preparation 121, 25.7 g, 0.1 mol) was dissolved in dry DMF (170 mL). POCl3 (46 g, 0.3 mol) was poured into this solution at 5-15° C., and the mixture was kept this temperature for 60 minutes. The resulting solution was slowly poured in portions into crushed ice (700 g) and stirred until a homogeneous solution was obtained. The solution was neutralized with a 20% aqueous K2CO3 solution to pH 7-8. The product was extracted with ethyl acetate. The organic extract was washed with brine and concentrated in vacuo to give a dark-brown liquid, which was purified by silica gel column chromatography eluting with EtOAc:Hexane 1:1 to afford the title compound as a colourless liquid (96%). Taken directly on to the next step.

Workup

  1. customfor 60 minutes
  2. additionThe resulting solution was slowly poured in portions
  3. customwas obtained
  4. extractionThe product was extracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with brine
  7. concentrationconcentrated in vacuo
  8. customto give a dark-brown liquid, which
  9. customwas purified by silica gel column chromatography
  10. washeluting with EtOAc:Hexane 1:1

Sources & evidence

ORD record
ord-881b00efb324449e90227b8e5a1ec89b
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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