Methanol → Methyl L-phenylalaninate hydrochloride

HRID 851459Notes

Reaction equation

HRID 851459 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.S(Cl)([Cl:15])=O.[CH3:17]O>>[NH2:1][C@H:2]([C:10]([O:12][CH3:17])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[ClH:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 6140L-PhenylalanineHCID 24386Thionyl Chloride

Product 1

HCID 75736Methyl L-phenylalaninate hydrochlorideYield 98%

Procedure

A suspension of 16.52 g (100 mmol) of L-phenylalanine in 200 ml of anhydrous methanol was cooled in a ice-salt bath. Thionyl chloride (23.8 g, 200 mmol) was added dropwise over a period of 30 minutes. After the addition was completed, cooling was stopped and the reaction mixture was stirred at 25° for 20 hours. After heating under reflux for 30 minutes, the solution was cooled and freed of solvent on a rotary evaporator under reduced pressure to yield 21.29 g (98%) of L-Phe-OMe-HCl. TLC: Rf 0.87 (10% MeOH in CHCl3, few drops of NH4OH).

Workup

  1. temperaturewas cooled in a ice-salt bath
  2. additionAfter the addition
  3. temperaturecooling
  4. temperatureAfter heating
  5. temperatureunder reflux for 30 minutes
  6. temperaturethe solution was cooled
  7. customfreed of solvent on a rotary evaporator under reduced pressure

Sources & evidence

ORD record
ord-d630e8e6153c457b9be0bbd5cd551722
Source dataset
uspto-grants-1983_05
Patent number
US04384994

Reaction notes

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