Methanol → O-benzyl-L-tyrosine

HRID 411876Notes

Reaction equation

HRID 411876 reaction equation
[NH2:1][C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.CO.[CH2:16](Cl)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[OH-].[Na+].S([O-])([O-])(=O)=O.[Cu+2]>[NH2:1][C@@H:2]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:8][CH:9]=1)[C:11]([OH:13])=[O:12]

Participants

6

Reactant 3

HCID 887MethanolHCID 6057L-TyrosineHCID 7503Benzyl Chloride

Product 1

HCID 725701O-benzyl-L-tyrosine

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of L-tyrosine of the formula (10) (250 g) in 2N NaOH solution (552 ml), copper sulphate solution (172 g of CuSO4 in 600 ml of water) was added and heated at 60° C. for 2 h. The reaction mixture was cooled to room temperature and methanol (2.5 L) and 2N NaOH (83 ml) was added and then benzyl chloride (15 ml) was added drop wise. The reaction mass was allowed to warm to room temperature. The precipitate was filtered and washed to give the title compound as white to off-white solid (260 g, 70%) (Ref: Bodansky & Bodansky pp50).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. temperatureto warm to room temperature
  3. filtrationThe precipitate was filtered
  4. washwashed

Sources & evidence

ORD record
ord-cef605ecb60348f2a0d855cf2b49e6f3
Source dataset
uspto-grants-2003_05
Patent number
US06559335B2

Reaction notes

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