p-Toluenesulfonic acid → tert-butyl N-[(1R)-1-(benzylcarbamoyl)-2-hydroxyethyl]carbamate

HRID 2093018Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2093018
[CH2:1]([NH:8][C:9](=[O:27])[CH:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:11][O:12][C@@H]1CCCCO1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:1]([NH:8][C:9](=[O:27])[C@H:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 86650906HCID 86650906, Verbindung

Produkt 1

HCID 46223140tert-butyl N-[(1R)-1-(benzylcarbamoyl)-2-hydroxyethyl]carbamateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 12.86 g of Intermediate 3 and 0.65 g of p-toluensulfonic acid in 100 mL of ethanol was heated at reflux temperature for 2 hours. The solvent was evaporated under vacuum and to the residue was added ethyl acetate (100 mL) which resulted in the precipitation of a white solid. The solvent was partially distilled and 150 mL of petroleum oil was added and stirred overnight. The solid was collected by filtration and dried yielding 6.5 g of the title compound as a white solid.

Aufarbeitung

  1. temperatureat reflux temperature for 2 hours
  2. customThe solvent was evaporated under vacuum and to the residue
  3. additionwas added ethyl acetate (100 mL) which
  4. customresulted in the precipitation of a white solid
  5. distillationThe solvent was partially distilled
  6. addition150 mL of petroleum oil was added
  7. filtrationThe solid was collected by filtration
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-a43af31cd39347c2b0373adb7e270e80
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08440861B2

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