Acetone → N-(4-Ethylbenzoyl)phenylalanine

HRID 1194791Notes

Reaction equation

HRID 1194791 reaction equation
[NH2:1][C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CC(C)=O.[CH2:17]([C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1)[CH3:18].Cl>[OH-].[Na+]>[CH2:17]([C:19]1[CH:27]=[CH:26][C:22]([C:23]([NH:1][C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[O:24])=[CH:21][CH:20]=1)[CH3:18]

Participants

6

Reactant 4

HCID 180Acetone2×HCID 313Hydrochloric AcidHCID 71567D-PhenylalanineHCID 853684-Ethylbenzoyl chloride

Product 1

HCID 129105N-(4-Ethylbenzoyl)phenylalanineYield 84.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

D-Phenylalanine 2 g (12 mmole) was dissolved in 10% aqueous sodium hydroxide solution (10 ml), and acetone (10 ml) was added. An acetone (5 ml) solution of 4-ethyl benzoyl choride (2.5 g, 15 mmole) and a 10% aqueous sodium hydroxide solution were added dropwise to the mixture obtained above while stirring and cooling with ice over 20 minutes, the reaction solution being maintained at pH 10. The reaction solution was returned to the room temperature, stirred for 3 hours, and made an acidic with a dilute hydrochloric acid solution to precipitate crystals. The crystals were filtered, washed with water and recrystallized from ethyl acetate to obtain N-(4-etylbenzoyl)-D-phenylalanine (3.0 g, yield 83%).

Workup

  1. customobtained above
  2. temperaturecooling with ice over 20 minutes
  3. temperaturethe reaction solution being maintained at pH 10
  4. customwas returned to the room temperature
  5. stirringstirred for 3 hours
  6. customto precipitate crystals
  7. filtrationThe crystals were filtered
  8. washwashed with water
  9. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4fb4a73965744606861db76598c60f0a
Source dataset
uspto-grants-1989_03
Patent number
US04816484

Reaction notes

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