Potassium Hydroxide → L-Phenylalanine

HRID 2254285Notes

Reaction equation

HRID 2254285 reaction equation
C[O:2][C:3](=[O:33])[C@H:4]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[NH:5]C(CC1N(CC2C=CC=CC=2Cl)C(SCCC)=NC=1)=O.[OH-].[K+]>C(O)C.O>[NH2:5][C@H:4]([C:3]([OH:33])=[O:2])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 54145803N-[{1-(2-chlorophenyl)methyl-2-propylthio-1H-imidazol-5-yl}methylcarbonyl]-L-phenylalanine methyl ester

Product 1

HCID 6140L-Phenylalanine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The methyl ester from Example 9 (i) (0.58 g, 1.2 mmol) was dissolved in ethanol (10 mL) and a solution of potassium hydroxide (0.223 g, 4 mmol) in water (4 mL) was added. This solution was stirred at room temperature for 1.5 hours. The ethanol was evaporated, the residue was diluted with water (10 mL) and the basic solution was extracted with ether. The aqueous layer was acidified to pH 3.5 with 10% hydrochloric acid solution, and the cooled suspension was then filtered, washed with water and dried in vacuum to provide 0.46 g (82%) of N-[1-(2-chlorophenyl)methyl-2-propylthio-1H-imidazol-5-yl}methylcarbonyl]-L-phenylalanine; mp 120°-121° C.

Workup

  1. customThe ethanol was evaporated
  2. additionthe residue was diluted with water (10 mL)
  3. extractionthe basic solution was extracted with ether
  4. filtrationthe cooled suspension was then filtered
  5. washwashed with water
  6. customdried in vacuum

Sources & evidence

ORD record
ord-5a3f3693207a458b910f049270af9f40
Source dataset
uspto-grants-1993_08
Patent number
US05234917

Reaction notes

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