Formaldehyde → N,N-Dimethyl-L-tyrosine methyl ester

HRID 1492896Notes

Reaction equation

HRID 1492896 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:15])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)N.[C:16](=O)(O)[O-].[Na+].C=O.[C:23]([BH3-])#[N:24].[Na+]>O.C(#N)C>[CH3:2][O:3][C:4](=[O:15])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)[N:24]([CH3:23])[CH3:16]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 76956Methyl tyrosinate hydrochlorideHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 54420482N,N-Dimethyl-L-tyrosine methyl esterYield 32.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of L-tyrosine methyl ester hydrochloride (1 g) in water (1.5 ml) was added sodium bicarbonate (0.363 g) under ice-cooling and stirred for 10 minutes, and then acetonitrile (7 ml), 37% formaldehyde aqueous solution (0.637 ml) and sodium cyanoborohydride (0.182 g) was added thereto at -5° C. The mixture was stirred for 2 hours at -5° C. The resultant insoluble material was filtered off, and the filtrate was extracted with ethyl acetate. The organic layer was separated and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give N,N-dimethyl-L-tyrosine methyl ester (0.21 g).

Workup

  1. temperaturecooling
  2. customat -5° C
  3. stirringThe mixture was stirred for 2 hours at -5° C
  4. filtrationThe resultant insoluble material was filtered off
  5. extractionthe filtrate was extracted with ethyl acetate
  6. customThe organic layer was separated
  7. dry with materialdried over magnesium sulfate
  8. filtrationThe magnesium sulfate was filtered off
  9. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-40339ac7fae94382a7cb80dd873497fa
Source dataset
uspto-grants-1994_12
Patent number
US05376634

Reaction notes

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