1-Butanol → L-Tyrosine, butanoate (ester)

HRID 2354534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2354534
[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.S(=O)(=O)(O)O.[CH2:19]([OH:23])[CH2:20][CH2:21][CH3:22]>O.C1(C)C=CC=CC=1>[C:19]([O:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][C@@H:2]([C:11]([OH:13])=[O:12])[NH2:1])=[CH:9][CH:8]=1)(=[O:23])[CH2:20][CH2:21][CH3:22]

Komponenten

6

Edukt 3

HCID 2631-ButanolHCID 1118Sulfuric AcidHCID 6057L-Tyrosine

Produkt 1

HCID 66739174L-Tyrosine, butanoate (ester)

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel

Versuchsvorschrift

18.19 g of tyrosine was suspended in a solution of 9.8 g of concentrated sulfuric acid, 40 mL water, 40 mL of butanol, and 200 mL of toluene in a 500 mL round bottom flask equipped with a condenser and a Dean-Stark apparatus. The resulting solution was heated at reflux temperature until no more water could be distilled. The resulting solution was cooled in an ice bath, which caused the solution to separate into two phases. The upper phase was discarded and the lower phase, an oily syrup, was retained. The syrup was mixed with sufficient 5% aqueous sodium bicarbonate solution to neutralize acidic impurities to provide a solid that was collected by filtration and washed with cold water. The resulting solid was re-crystallized in ethyl acetate.

Aufarbeitung

  1. customequipped with a condenser
  2. temperatureThe resulting solution was heated
  3. distillationcould be distilled
  4. temperatureThe resulting solution was cooled in an ice bath
  5. customto separate into two phases
  6. additionThe syrup was mixed with sufficient 5% aqueous sodium bicarbonate solution
  7. customto provide a solid
  8. filtrationthat was collected by filtration
  9. washwashed with cold water
  10. customThe resulting solid was re-crystallized in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-31b0bc809d6c423f92b9e69b1f5f39d2
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754679B2

Notizen zur Reaktion

Wird geladen…