Tyramine → HCID 22823205, compound

HRID 851309Notes

Reaction equation

HRID 851309 reaction equation
ClC(OCC)=O.[NH:7](C(OCC1C=CC=CC=1)=O)[C@H:8]([C:10](O)=[O:11])[CH3:9].CN1CCOCC1.[NH2:30][CH2:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1.[H][H]>C1COCC1.CN(C=O)C.C(O)C.[C].[Pd]>[OH:39][C:36]1[CH:37]=[CH:38][C:33]([CH2:32][CH2:31][NH:30][C:10](=[O:11])[C@H:8]([CH3:9])[NH2:7])=[CH:34][CH:35]=1

Participants

10

Reactant 5

HCID 5610TyramineHCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 736104N-carbobenzyloxyalanineHCID 178418361HCID 178418361, compound

Product 1

HCID 22823205HCID 22823205, compound

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

Ethyl chloroformate (0.94 ml) was added to Z-Ala-OH (2.2 g, 10 mM) and NMM (1.0 g, 10 mM) in THF at -20° C. and the mixture was stirred at -15° C. for 2 minutes. Tyramine (1.4 g, 10 mM) in DMF (20 ml) was added thereto and the mixture was stirred at room temperature overnight. THF was distilled off and ethyl acetate (100 ml) was added. The solution was washed with 10% w/w aqueous citrate, 5% w/w aqueous sodium bicarbonate and a small amount of water and dried with anhydrous sodium sulfate. After the drying agent was removed, n-hexane was added to the oily residue obtained from the concentrated solution. The precipitate was recrystallized from ethyl acetate-n-hexane to obtain a white powder. This powder was dissolved in 50% aqueous ethanol (600 ml), 5% palladium carbon (600 mg) and N-HCl (5 ml) were added, and hydrogen gas was introduced with stirring at room temperature. After the generation of carbon dioxide has terminated, the catalyst was removed and the filtrate was concentrated and dried in vacuo to yield L-alanine-p-hydroxyphenylethylamide.HCl (1.1 g, 46.1%).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. distillationTHF was distilled off
  3. additionethyl acetate (100 ml) was added
  4. washThe solution was washed with 10% w/w aqueous citrate, 5% w/w aqueous sodium bicarbonate
  5. dry with materiala small amount of water and dried with anhydrous sodium sulfate
  6. customAfter the drying agent was removed
  7. additionn-hexane was added to the oily residue
  8. customobtained from the concentrated solution
  9. customThe precipitate was recrystallized from ethyl acetate-n-hexane
  10. customto obtain a white powder
  11. stirringwith stirring at room temperature
  12. customAfter the generation of carbon dioxide has terminated
  13. customthe catalyst was removed
  14. concentrationthe filtrate was concentrated
  15. customdried in vacuo

Sources & evidence

ORD record
ord-6228122688374562be3f82a2ce163546
Source dataset
uspto-grants-1983_05
Patent number
US04384041

Reaction notes

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