Sodium Iodide → L-Tyrosine

HRID 2091435Notes

Reaction equation

HRID 2091435 reaction equation
C[O:2][C:3](=[O:14])[C@H:4]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[NH2:5].CON(C1C=CC=CC=1)[C@H](C(O)=O)C.N[C@H](C(O)=O)C.[I-].[Na+]>Cl.Br>[NH2:5][C@H:4]([C:3]([OH:14])=[O:2])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 5950L-AlanineHCID 70652Tyrosine Methyl EsterHCID 54118972HCID 54118972, compound

Product 1

HCID 6057L-Tyrosine

Reagents, catalysts & solvents 2

HCID 260Hydrogen BromideSolventHCID 313Hydrochloric AcidSolvent

Conditions

Temperature
105 °C

Procedure

The synthesis was carried out with reference to the disclosure of Reference Article (8). There was dissolved 1.02 g (3.8 mmol) of the tyrosine methyl ester (25) in 50 ml of a 1N HCl solution, and then the resulting solution was stirred at 105° C. for 12 hours. After cooling, the resulting mixture was concentrated and then ion-exchanged using Dowex-50w-X8 to thus give 775 mg (3.77 mmol) of methoxyphenyl alanine. This alanine and 623 mg (4.15 mmol) of sodium iodide were dissolved in 45 ml of a 48% hydrobromic acid solution, the container was closed with a septum and firmly tightened with a wire and the content thereof was stirred at 92° C. for 4 hours. After cooling down to room temperature, the resulting mixture was concentrated and then ion-exchanged using Dowex-50w-X8 to thus give the title compound: tyrosine (4).

Workup

  1. temperatureAfter cooling
  2. concentrationthe resulting mixture was concentrated
  3. customthe container was closed with a septum
  4. stirringthe content thereof was stirred at 92° C. for 4 hours
  5. temperatureAfter cooling down to room temperature
  6. concentrationthe resulting mixture was concentrated

Sources & evidence

ORD record
ord-4c6b2fc78173431193b95ae14a726793
Source dataset
uspto-grants-2013_05
Patent number
US08440169B2

Reaction notes

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