Triethylamine → O-benzyl-N-trifluoroacetyltyrosine

HRID 1938114Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1938114
[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]([CH2:13][C@@H:14]([C:16]([OH:18])=[O:17])[NH2:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C([O:30][C:31](=O)[C:32]([F:35])([F:34])[F:33])C>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][C@@H:14]([C:16]([OH:18])=[O:17])[NH:15][C:31](=[O:30])[C:32]([F:35])([F:34])[F:33])=[CH:19][CH:20]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 725701O-benzyl-L-tyrosine

Produkt 1

HCID 53698430O-benzyl-N-trifluoroacetyltyrosine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

112.5 g (0.41 mmol) of O-benzyltyrosine is suspended in 1 liter of dry methanol and combined at room temperature with 58.9 ml (0.42 mol) of triethylamine. After adding 67 ml (0.53 mol) of trifluoroacetic acid ethyl ester, the mixture is stirred at room temperature for 130 hours under exclusion of moisture. The mixture is separated from unreacted starting material and volatile components are removed by shaking with ethyl acetate/aqueous hydrochloric acid. The ethyl acetate phase is decolorized with activated carbon. Evaporation of the solvents yields 120.7 g (80% of theory) of colorless crystals.

Aufarbeitung

  1. customThe mixture is separated
  2. customare removed
  3. stirringby shaking with ethyl acetate/aqueous hydrochloric acid
  4. customEvaporation of the solvents
  5. customyields 120.7 g (80% of theory) of colorless crystals

Quellen und Nachweise

ORD-Eintrag
ord-f37a66fe8f75498ba3931facae87b639
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05693309

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