Reaktion #86610

ord-53df29585d21450a8c370070197b12a9

Reaktionsgleichung

CN(CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1)C(=O)CN(C)/C(=N/C(=O)OC(C)(C)C)NC(=O)OC(C)(C)C.O=C([O-])C(F)(F)F
N2—{(E)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}-N,N2-dimethyl-N-[3-(triphenylphosphonio)propyl]glycinamide trifluoroacetate
→
CN(CC(=O)N(C)CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1)C(=N)[NH3+].O=C([O-])C(F)(F)F.O=C([O-])C(F)(F)F
title compound
Ausbeute 18.0%
CN(CC(=O)N(C)CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1)C(=N)[NH3+].O=C([O-])C(F)(F)F.O=C([O-])C(F)(F)F
N2-[ammonio(imino)methyl]-N,N2-dimethyl-N-[3-(triphenylphosphonio)propyl]glycinamide bis(trifluoroacetate)
Ausbeute 18.0%

Edukte

CN(CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1)C(=O)CN(C)/C(=N/C(=O)OC(C)(C)C)NC(=O)OC(C)(C)C.O=C([O-])C(F)(F)F
N2—{(E)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}-N,N2-dimethyl-N-[3-(triphenylphosphonio)propyl]glycinamide trifluoroacetate

Reagenzien

Keine

Lösungsmittel

O=C(O)C(F)(F)F
trifluoroacetic acid

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe crude was isolated upon removal of volatiles
  2. 2
    SonstigePurification by preparative HPLC

Vorschrift

N2—{(E)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}-N,N2-dimethyl-N-[3-(triphenylphosphonio)propyl]glycinamide trifluoroacetate (330 mg, 0.43 mmol) was dissolved in trifluoroacetic acid (1.6 ml) and stirred at room temperature for 15 minutes, and the crude was isolated upon removal of volatiles. Purification by preparative HPLC to give the title compound as a white solid following lyophilization (18% yield).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09434753B2uspto-grants-2016_09