Methanol → Methyl L-phenylalaninate hydrochloride

HRID 2379641Notes

Reaction equation

HRID 2379641 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>>[ClH:15].[CH3:17][O:11][C:10](=[O:12])[C@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[NH2:1]

Participants

4

Reactant 3

HCID 887MethanolHCID 6140L-PhenylalanineHCID 24386Thionyl Chloride

Product 1

HCID 75736Methyl L-phenylalaninate hydrochloride

Procedure

A 400 g (2.42 mol) sample of L-phenylalanine was slurried in 4 L of MeOH. To this was slowly added 240 mL of thionyl chloride, the temperature was allowed to increase, and the solution held at reflux for 16 hours. The solvent was removed to afford the title product as a white solid. The compound was taken directly to the next step.

Workup

  1. temperatureto increase
  2. temperatureat reflux for 16 hours
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-f1047f119c99434f9740762b993aa0f6
Source dataset
uspto-grants-1994_11
Patent number
US05362912

Reaction notes

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