Methanol → HCID 70061470, compound

HRID 2230294Notes

Reaction equation

HRID 2230294 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.Br[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=1>[OH-].[Na+].O.[O-]S([O-])(=O)=O.[Cu+2]>[NH2:1][C@@H:2]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)=[CH:8][CH:9]=1)[C:11]([OH:13])=[O:12]

Participants

7

Reactant 3

HCID 887MethanolHCID 6057L-TyrosineHCID 7721p-Xylyl bromide

Product 1

HCID 70061470HCID 70061470, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent2×

Conditions

Temperature
60 °C

Procedure

A mixture of tyrosine (1.83 g, 10 mmol) and CuSO4 (0.81 g, 5 mmol) in 10 mL of 2N NaOH and 5 mL H2O was heated to 60° C. and cooled to room temperature. The reaction mixture was treated with MeOH (35 mL) and 2N NaOH (1.5 mL) followed by α-bromo-p-xylene. The resulting mixture was stirred at 25° C. for 2 hours and filtered. The solid obtained was washed with a 17.5:5 H2O/MeOH solution followed by MeOH. The solid was triturated with 1N HCl (3×10 mL), H2O (2×5 mL), 1.5N NH4OH solution (3×10 mL), and H2O (2×5 mL). The solid obtained was dried overnight under vacuum to give the title compound as a solid (1.99 g, 70%).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customThe solid obtained
  4. washwas washed with a 17.5:5 H2O/MeOH solution
  5. customThe solid was triturated with 1N HCl (3×10 mL), H2O (2×5 mL), 1.5N NH4OH solution (3×10 mL), and H2O (2×5 mL)
  6. customThe solid obtained
  7. customwas dried overnight under vacuum

Sources & evidence

ORD record
ord-ac41cc469a1845a5bfc246ed8ba1fec7
Source dataset
uspto-grants-2002_07
Patent number
US06423689B1

Reaction notes

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