Methanol → O-benzyl-L-tyrosine

HRID 1861552Notes

Reaction equation

HRID 1861552 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](Br)[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 7498Benzyl Bromide

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 (21) (18.1 g) in 2N NaOH solution (115 ml), copper sulphate solution (12.5 g of CuSO4 in 50 ml of water) was added and heated at 60° C. for 1.5 h. The reaction mixture was cooled to room temperature and methanol (350 ml) and 2N NaOH (12.5 ml) was added and then benzyl bromide (12 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 (18.5 g, 66.8%) (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-4e162a24d18844ee89431eadf0d74ac9
Source dataset
uspto-grants-2003_03
Patent number
US06531596B1

Reaction notes

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