Reaktion #86609

ord-2552db1de1a3438f89394ff526568560

Reaktionsgleichung

CN(CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1)C(=O)CN(C)C(=O)OC(C)(C)C.[Br-]
N2-(tert-butoxycarbonyl)-N,N2-dimethyl-N-[3-(triphenylphosphonio)propyl]glycinamide bromide
O=C(O)C(F)(F)F
trifluoroacetic acid
→
CNCC(=O)N(C)CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C([O-])C(F)(F)F
title compound
CNCC(=O)N(C)CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.O=C([O-])C(F)(F)F
N,N2-dimethyl-N-[3-(triphenylphosphonio)propyl]-glycinamide trifluoroacetate

Edukte

CN(CCC[P+](c1ccccc1)(c1ccccc1)c1ccccc1)C(=O)CN(C)C(=O)OC(C)(C)C.[Br-]
N2-(tert-butoxycarbonyl)-N,N2-dimethyl-N-[3-(triphenylphosphonio)propyl]glycinamide bromide
O=C(O)C(F)(F)F
trifluoroacetic acid

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe volatiles were removed under high vacuum
  2. 2
    Waschenwashed with aqueous NaHCO3
  3. 3
    WaschenThe organic layer was then washed with water
  4. 4
    Einengenconcentrated

Vorschrift

N2-(tert-butoxycarbonyl)-N,N2-dimethyl-N-[3-(triphenylphosphonio)propyl]glycinamide bromide (280 mg, 0.48 mmol) was dissolved in trifluoroacetic acid (1.9 mL, 25 mol) at room temperature. After 30 minutes, the volatiles were removed under high vacuum and the crude product taken up in methylene chloride and washed with aqueous NaHCO3. The organic layer was then washed with water and concentrated to give the title compound in quantitative yield.

Quelle

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