StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Benzyl chloroformate → 3-(1,1-Dimethylethyl)-N-[(phenylmethoxy)carbonyl]-L-tyrosine methyl ester

HRID 1383714
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1383714
[NH2:1][C@H:2]([C:15]([O:17][CH3:18])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.C([O-])(O)=O.[Na+].[CH:24]1[CH:29]=[CH:28][C:27]([CH2:30][O:31][C:32](Cl)=[O:33])=[CH:26][CH:25]=1>O.C(OCC)(=O)C>[NH:1]([C:32]([O:31][CH2:30][C:27]1[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=1)=[O:33])[C@H:2]([C:15]([O:17][CH3:18])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:12])[CH3:13])[CH:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 15549498Tyr(3-tBu)-OMe

Produkt 1

HCID 155494893-(1,1-Dimethylethyl)-N-[(phenylmethoxy)carbonyl]-L-tyrosine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel
HCID 8857
Ethyl Acetate
Lösungsmittel

Versuchsvorschrift

To a solution of Tyr(3-tBu)-OMe (1.1 g) in H2O (10 ml), 0.7 g (6.57 mmol) of NaHCO3 and 0.92 ml (6.57 mmol) of Z-Cl were added under cooling with ice and the mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ethyl acetate and washed with water and saturated brine. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate:n-hexane=1:2) to give Z-Tyr(3-t-Bu)-OMe in the amount of 1.44 g (85%).

Aufarbeitung

  1. temperatureunder cooling with ice
  2. washwashed with water and saturated brine
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washThe resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate:n-hexane=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-d006d3b48f524eaca4b4f1d340b12881
Quelldatensatz
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06255285B1

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion