L-Tryptophan → Tryptophan butyl ester

HRID 80946

Reaktionsgleichung

Reaktionsgleichung von HRID 80946
[NH2:1][C@H:2]([C:13]([OH:15])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.S(Cl)(Cl)=O>C(O)CCC>[CH2:13]([O:14][C:13](=[O:15])[C@H:2]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)[NH2:1])[CH2:2][CH2:3][CH3:4]

Komponenten

4

Edukt 2

HCID 6305L-TryptophanHCID 24386Thionyl Chloride

Produkt 1

HCID 11666077Tryptophan butyl esterAusbeute 181,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

L-Tryptophane (5 g; 24.5 mmol) and thionyl chloride (73.5 mmol; 5.3 ml) were dissolved in n-butanol (80 ml) and stirred at 100° C. over night. The product 5 precipitated after cooling to room temperature, was filtered off and washed with ice cold butanol and petrol ether. The product was dried at the oil pump, yielding 5.8 g of 5 (91%).

Aufarbeitung

  1. customThe product 5 precipitated
  2. temperatureafter cooling to room temperature
  3. filtrationwas filtered off
  4. washwashed with ice cold butanol and petrol ether
  5. customThe product was dried at the oil pump

Quellen und Nachweise

ORD-Eintrag
ord-4ed8fe63fe6941eca33ae882bbf034d6
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846682B2

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