Water → N-(2-methoxybenzoyl)dehydroalanine

HRID 362753Notes

Reaction equation

HRID 362753 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([NH2:7])=[O:6].[C:12]([OH:17])(=[O:16])[C:13]([CH3:15])=O.O>ClCCCl>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([NH:7][C:13]([C:12]([OH:17])=[O:16])=[CH2:15])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 1060Pyruvic AcidHCID 755402-Methoxybenzamide

Product 1

HCID 15342116N-(2-methoxybenzoyl)dehydroalanineYield 8.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A suspension of 2-methoxybenzamide in 1,2-di-chloroethane (24.5 ml/g) is brought to reflux in the presence of 3 equivalents of freshly distilled pyruvic acid in a round-bottomed flask surmounted by a system which makes it possible to remove the water formed during the reaction. When the formation of water has finished 15 (approximately 7 hours), the reaction mixture is left at room temperature. After filtering off the insoluble materials, the filtrate is extracted with an aqueous sodium bicarbonate solution. The combined aqueous phases are extracted with dichloromethane and then acidified with hydrochloric acid. The precipitate formed is filtered off, dried and then taken up in ethyl acetate. After filtering off the insoluble material, the filtrate is concentrated under vacuum, dissolved in dichloromethane and then precipitated with heptane, thus providing pure N-(2-methoxybenzoyl)dehydroalanine. (Nonoptimized yield 8.5%).

Workup

  1. customto remove the water
  2. customformed during the reaction
  3. custom15 (approximately 7 hours)
  4. waitthe reaction mixture is left at room temperature
  5. filtrationAfter filtering off the insoluble materials
  6. extractionthe filtrate is extracted with an aqueous sodium bicarbonate solution
  7. extractionThe combined aqueous phases are extracted with dichloromethane
  8. customThe precipitate formed
  9. filtrationis filtered off
  10. customdried
  11. filtrationAfter filtering off the insoluble material
  12. concentrationthe filtrate is concentrated under vacuum
  13. dissolutiondissolved in dichloromethane
  14. customprecipitated with heptane

Sources & evidence

ORD record
ord-af29afb8d74040a291fcaad76ba4a437
Source dataset
uspto-grants-1999_02
Patent number
US05871755

Reaction notes

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