Reaktion #747946

ord-d4b869541ab64a34be7236b77e328d2d

Reaktionsgleichung

COC(=O)CN(c1ccc(OCC(=O)OCC[Si](C)(C)C)cc1OCc1ccccc1)S(=O)(=O)NC(=O)OC(C)(C)C
methyl N-(2-(benzyloxy)-4-{2-oxo-2-[2-(trimethylsilyl)ethoxy]ethoxy}phenyl)-N-{[(tert-butoxycarbonyl)amino]sulfonyl}glycinate
→
COC(=O)CN(c1ccc(OCC(=O)OCC[Si](C)(C)C)cc1OCc1ccccc1)S(N)(=O)=O
title compound
COC(=O)CN(c1ccc(OCC(=O)OCC[Si](C)(C)C)cc1OCc1ccccc1)S(N)(=O)=O
Methyl N-(aminosulfonyl)-N-(2-(benzyloxy)-4-{2-oxo-2-[2-(trimethylsilyl)ethoxy]ethoxy}phenyl)glycinate

Edukte

COC(=O)CN(c1ccc(OCC(=O)OCC[Si](C)(C)C)cc1OCc1ccccc1)S(=O)(=O)NC(=O)OC(C)(C)C
methyl N-(2-(benzyloxy)-4-{2-oxo-2-[2-(trimethylsilyl)ethoxy]ethoxy}phenyl)-N-{[(tert-butoxycarbonyl)amino]sulfonyl}glycinate

Reagenzien

Keine

Lösungsmittel

C1COCCO1.Cl
HCl dioxane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe solvent is removed under reduced pressure and water
  2. 2
    workup.ADDITIONis added
  3. 3
    ExtraktionThe mixture is extracted with EtOAc
  4. 4
    Trocknenthe organic phase dried over magnesium sulfate
  5. 5
    SonstigeThe solvent is removed under reduced pressure

Vorschrift

A mixture of methyl N-(2-(benzyloxy)-4-{2-oxo-2-[2-(trimethylsilyl)ethoxy]ethoxy}phenyl)-N-{[(tert-butoxycarbonyl)amino]sulfonyl}glycinate (50 mg, 0.08 mmol) in HCl/dioxane (3 mL, 4.0 M) is stirred at RT for 30 min. The solvent is removed under reduced pressure and water is added. The mixture is extracted with EtOAc and the organic phase dried over magnesium sulfate. The solvent is removed under reduced pressure to give the title compound.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08084448B2uspto-grants-2011_12