Glycine → O-methoxymethyl-beta-hydroxytyrosine

HRID 1648174Notes

Reaction equation

HRID 1648174 reaction equation
[OH-].[K+].[NH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH3:8][O:9][CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1>C(O)C>[CH3:8][O:9][CH2:10][O:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]([OH:17])[C@@H:4]([C:5]([OH:7])=[O:6])[NH2:3])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 750GlycineHCID 14797Potassium HydroxideHCID 2500744-(Methoxymethoxy)benzaldehyde

Product 1

HCID 54167947O-methoxymethyl-beta-hydroxytyrosineYield 19.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of potassium hydroxide (26.8 g) in ethanol (500 ml) was added glycine (14.6 g) and 4-methoxymethoxybenzaldehyde (48.5 g) at room temperature. After stirring for 19 hours, the solvent was removed in vacuo. The residue was dissolved in water and acidified with hydrochloric acid. The solution was washed with ethyl acetate and adjusted to pH 6.0 with sodium bicarbonate. White solid was precipitated and collected to give O-methoxymethyl-β-hydroxytyrosine (9.2 g).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in water
  3. washThe solution was washed with ethyl acetate
  4. customWhite solid was precipitated
  5. customcollected

Sources & evidence

ORD record
ord-cde470487215418c8df1b92e55c6603a
Source dataset
uspto-grants-1995_07
Patent number
US05436140

Reaction notes

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