Reaktion #747948

ord-fc292e2d4be547bfae4106283a955beb

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
→
C[Si](C)(C)CCOC(=O)COc1ccc(N(CC(=O)O)S(N)(=O)=O)c(OCc2ccccc2)c1
title compound
C[Si](C)(C)CCOC(=O)COc1ccc(N(CC(=O)O)S(N)(=O)=O)c(OCc2ccccc2)c1
N-(Aminosulfonyl)-N-(2-(benzyloxy)-4-{2-oxo-2-[2-(trimethylsilyl)ethoxy]ethoxy}phenyl)glycine

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

ClCCl.O=C(O)C(F)(F)F
TFA methylene chloride

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe solvent is removed under reduced pressure
  2. 2
    workup.DISSOLUTIONthe residue is dissolved in methylene chloride
  3. 3
    Sonstigethe solvent evaporated (4×)

Vorschrift

A solution of methyl N-(2-(benzyloxy)-4-{2-oxo-2-[2-(trimethylsilyl)ethoxy]ethoxy}phenyl)-N-{[(tert-butoxycarbonyl)amino]sulfonyl}glycinate (1.15 g, 1.84 mmol) in 20 mL of TFA/methylene chloride (1:1) is stirred at RT for 30 min. The solvent is removed under reduced pressure and the residue is dissolved in methylene chloride and the solvent evaporated (4×) to give the title compound.

Quelle

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