L-Phenylalanine → N-(4-Phenylbutanoyl)-L-phenylalanine

HRID 1906143Notes

Reaction equation

HRID 1906143 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.[C:13]([O-:16])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl.O>[C:4]1([CH2:3][CH2:2][CH2:10][C:13]([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:16])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 6140L-PhenylalanineHCID 10340Sodium Carbonate

Product 1

HCID 13488126N-(4-Phenylbutanoyl)-L-phenylalanineYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

The above mentioned ester (13 g) was dissolved in chloroform (200 ml). This solution was added dropwise to the solution obtained by dissolving L-phenylalanine (16.5 g) and Na2CO3 (15.9 g) in water (150 ml) while stirring at room temperature. After that, the mixture was stirred for 7 hours and the insoluble matter thus produced was removed by filtration. The filtrate was acidified to pH 1.0 with 6N HCl. The precipitated crystals were filtered, washed with water, and re-crystallized from 90% aqueous methanol to obtain N-(4-phenylbutyroyl)-L-phenylalanine (11.2 g) having melting point: 178° C.

Workup

  1. additionThis solution was added dropwise to the solution
  2. customobtained
  3. stirringAfter that, the mixture was stirred for 7 hours
  4. customthe insoluble matter thus produced
  5. customwas removed by filtration
  6. filtrationThe precipitated crystals were filtered
  7. washwashed with water
  8. customre-crystallized from 90% aqueous methanol

Sources & evidence

ORD record
ord-57912a5b794c49c7b51b90b114bdfb19
Source dataset
uspto-grants-1987_03
Patent number
US04650785

Reaction notes

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