Water → HCID 53730131, compound

HRID 746022Notes

Reaction equation

HRID 746022 reaction equation
C(=O)([O-])O.[Na+].Cl.[NH2:7][CH:8]([C:13](=[O:16])[CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10].O.[C:18](Cl)(=[O:27])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(OCC)(=O)C>[C:18]([NH:7][CH:8]([C:13](=[O:16])[CH2:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10])(=[O:27])[CH:19]=[CH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 660233-Phenylprop-2-enoyl chlorideHCID 516892Sodium BicarbonateHCID 23311259HCID 23311259, compound

Product 1

HCID 53730131HCID 53730131, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Sodium hydrogen carbonate (10.0 g) was added to a mixture of methyl 2-amino-3-oxovalerate hydrochloride (9.1 g), ethyl acetate (50 ml) and water (40 ml) with ice-cooling and stirring followed by dropwise addition of a solution of cinnamoyl chloride (8.3 g) in ethyl acetate (10 ml). The whole mixture was stirred under ice-cooling for 2 hours and the ethyl acetate layer was separated. The aqueous layer was extracted with ethyl acetate. The ethyl acetate layers were combined, washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off and isopropyl ether was added to the residue to give methyl 2-cinnamoylamino-3-oxovalerate as crystals; yield 8.8 g (63.8%). Recrystallization from ethanol gave colorless needles melting at 119°-120° C.

Workup

  1. temperaturecooling
  2. stirringThe whole mixture was stirred under ice-
  3. temperaturecooling for 2 hours
  4. customthe ethyl acetate layer was separated
  5. extractionThe aqueous layer was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was then distilled off
  9. additionisopropyl ether was added to the residue

Sources & evidence

ORD record
ord-31414afa27f5402da0638b94b780e102
Source dataset
uspto-grants-1986_07
Patent number
US04602027

Reaction notes

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