Reaction #46325

ord-733fefb0a17c4d6aa12ad2ef65fce39e

Reaction equation

N[C@@H](Cc1ccccc1)C(=O)O
L-phenylalanine
N[C@@H](Cc1ccc(O)cc1)C(=O)O
L-tyrosine
Cl
HCl
→
CC(C)OC(=O)[C@@H](N)Cc1ccccc1.Cl
L-phenylalanine isopropyl ester hydrochloride
CC(C)OC(=O)[C@@H](N)Cc1ccc(O)cc1.Cl
L-tyrosine isopropyl ester hydrochloride

Reactants

N[C@@H](Cc1ccccc1)C(=O)O
L-phenylalanine
N[C@@H](Cc1ccc(O)cc1)C(=O)O
L-tyrosine
Cl
HCl

Reagents

None

Solvents

CC(C)O
isopropanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe mixture was heated
  2. 2
    Temperatureto reflux for 16 h
  3. 3
    Otherthe volatiles were evaporated under vacuum

Procedure

Excess HCl gas was added with stirring to a suspension of L-phenylalanine or L-tyrosine in excess isopropanol. The mixture was heated to reflux for 16 h, and then the volatiles were evaporated under vacuum to give L-phenylalanine isopropyl ester hydrochloride or L-tyrosine isopropyl ester hydrochloride of sufficient purity for immediate use.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07741328B2uspto-grants-2010_06