Dichloromethane → HCID 54555293, compound

HRID 746026Notes

Reaction equation

HRID 746026 reaction equation
[C:1](Cl)(=O)OCC.[C:7]([OH:17])(=O)[CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.ClCCl.[CH3:21][O:22][C:23]([CH2:25][C@H:26]([NH2:30])[C:27](O)=[O:28])=[O:24].Cl>C(N(CC)CC)C>[C:7]([NH:30][CH:26]([C:27](=[O:28])[CH3:1])[CH2:25][C:23]([O:22][CH3:21])=[O:24])(=[O:17])[CH:8]=[CH:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 87842-Propenoic acid, 3-phenyl-HCID 10928Ethyl chloroformateHCID 12832742L-Aspartic acid, 4-methyl ester, hydrochloride (1:1)

Product 1

HCID 54555293HCID 54555293, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent2×

Procedure

Ethyl chlorocarbonate (2.0 ml) was added dropwise to a mixture of cinnamic acid (2.96 g), dichloromethane (60 ml) and triethylamine (2.8 ml) under cooling with ice-sodium chloride and stirring, and the whole mixture was stirred for 10 minutes. L-Aspartic acid β-methyl ester hydrochloride (3.67 g) was added and triethylamine (5.6 ml) was further added dropwise. The resulting mixture was stirred at room temperature for 40 minutes, washed with 2N hydrochloric acid and water and dried over anhydrous magnesium sulfate. The solvent was then distilled off. To the thus-obtained N-cynnamoyl-L-aspartic acid β-methyl ester were added acetic anhydride (15 ml), triethylamine (15 ml) and 4-dimethylaminopyridine (0.2 g) and the mixture was stirred for 30 minutes, poured into water, stirred for 10 minutes for decomposition and extracted with ethyl acetate. The ethyl acetate layer was washed with diluted hydrochloric acid, water, aqueous sodium hydrogen carbonate and water, and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was treated with isopropyl ether to give methyl 3-cinnamoylamino- 4-oxovalerate as crystals; yield 2.65 g (48.1%). Recrystallization from ethyl ether gave colorless needles melting at 82°-83° C.

Workup

  1. stirringthe whole mixture was stirred for 10 minutes
  2. stirringThe resulting mixture was stirred at room temperature for 40 minutes
  3. washwashed with 2N hydrochloric acid and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was then distilled off
  6. additionTo the thus-obtained N-cynnamoyl-L-aspartic acid β-methyl ester were added acetic anhydride (15 ml), triethylamine (15 ml) and 4-dimethylaminopyridine (0.2 g)
  7. stirringthe mixture was stirred for 30 minutes
  8. additionpoured into water
  9. stirringstirred for 10 minutes for decomposition
  10. extractionextracted with ethyl acetate
  11. washThe ethyl acetate layer was washed with diluted hydrochloric acid, water, aqueous sodium hydrogen carbonate and water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. distillationThe solvent was distilled off
  14. additionthe residue was treated with isopropyl ether

Sources & evidence

ORD record
ord-921e11b5bc034a009248ae6de6266c87
Source dataset
uspto-grants-1986_07
Patent number
US04602027

Reaction notes

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