Hydrochloric Acid → O-methoxymethyl-N-methyl-beta-hydroxytyrosine

HRID 1648175Notes

Reaction equation

HRID 1648175 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:17]=[CH:16][C:8]([CH:9]([OH:15])[C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])=[CH:7][CH:6]=1.[CH3:18]OS(OC)(=O)=O.Cl>[OH-].[Na+]>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH:9]([OH:15])[C@@H:10]([C:12]([OH:14])=[O:13])[NH:11][CH3:18])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6497Dimethyl SulfateHCID 54167947O-methoxymethyl-beta-hydroxytyrosine

Product 1

HCID 53901170O-methoxymethyl-N-methyl-beta-hydroxytyrosineYield 23.4%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of O-methoxymethyl-β-hydroxytyrosine (21.0 g) in 1N-sodium hydroxide (250 ml) was added dimethylsulfate (16.5 g). After stirring for 20 min. at 90° C., the solution was acidified with diluted hydrochloric acid in ice bath. The acidic solution was washed with diethyl ether and adjusted to pH 6.0 with 1N-sodium hydroxide. After evaporation, the solid was collected by filtration to give O-methoxymethyl-N-methyl-β-hydroxytyrosine (5.2 g).

Workup

  1. washThe acidic solution was washed with diethyl ether
  2. customAfter evaporation
  3. filtrationthe solid was collected by filtration

Sources & evidence

ORD record
ord-b984659af4614e0da22ba228b911d784
Source dataset
uspto-grants-1995_07
Patent number
US05436140

Reaction notes

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