L-Phenylalanine → Benzyl L-phenylalaninate hydrochloride (1:1)

HRID 1288437Notes

Reaction equation

HRID 1288437 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.[CH2:13]([Cl:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CS(C)=O>[ClH:20].[NH2:1][C@H:2]([C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 6140L-PhenylalanineHCID 7503Benzyl Chloride

Product 1

HCID 12636208Benzyl L-phenylalaninate hydrochloride (1:1)

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1.65 g. (10 mmole) of racemic phenylalanine and 1.27 g. (10 mmole) of benzyl chloride in 10 ml. dimethylsulfoxide is stirred at 60° C. for 7 hours and then allowed to cool. Dimethylsulfoxide is removed by stirring four times with 25 ml. ethyl ether and then decanting off the ethyl ether. The residue is stirred with 25 ml. hot ethanol, filtered from some insoluble solid and the filtrate diluted with 100 ml. ethyl ether to precipitate the ester hydrochloride. After filtering and drying, essentially pure benzyl phenylalaninate hydrochloride is obtained. Recrystallization from a warm mixture of 8 ml. water and 1 ml. 0.1 N hydrochloric acid gives an analytical sample, m.p. 190.5-192.5° C.

Workup

  1. additionA mixture of 1.65 g
  2. temperatureto cool
  3. customDimethylsulfoxide is removed
  4. customethyl ether and then decanting off the ethyl ether
  5. stirringThe residue is stirred with 25 ml
  6. filtrationhot ethanol, filtered from some insoluble solid
  7. additionthe filtrate diluted with 100 ml
  8. customethyl ether to precipitate the ester hydrochloride
  9. filtrationAfter filtering
  10. customdrying

Sources & evidence

ORD record
ord-c84e9f35e8d5435f92ec98cb6c767324
Source dataset
uspto-grants-1976_10
Patent number
US03988341

Reaction notes

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