Reaktion #1996

ord-e9a35b5778f84e018ef46a7daf51dbfd

Reaktionsgleichung

CCOC(=O)c1cc(C2CC2)c2c(C)c(C3(C(=O)O)CC3)c(F)cn2c1=O
product
CCOC(=O)c1cc(C2CC2)c2c(C)c(C3(C(=O)O)CC3)c(F)cn2c1=O
1-cyclopropyl-8-(1-hydroxycarbonyl-1-cyclopropyl)-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester
[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1
diphenylphosphoryl azide
CC(C)(C)O
t-butanol
CCN(CC)CC
triethylamine
→
CCOC(=O)c1cc(C2CC2)c2c(C)c(C3(NC(=O)OC(C)(C)C)CC3)c(F)cn2c1=O
1-cyclopropyl-8-(1-Bocamino-1-cyclopropyl)-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester

Edukte

CCOC(=O)c1cc(C2CC2)c2c(C)c(C3(C(=O)O)CC3)c(F)cn2c1=O
product
CCOC(=O)c1cc(C2CC2)c2c(C)c(C3(C(=O)O)CC3)c(F)cn2c1=O
1-cyclopropyl-8-(1-hydroxycarbonyl-1-cyclopropyl)-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester
[N-]=[N+]=NP(=O)(c1ccccc1)c1ccccc1
diphenylphosphoryl azide
CC(C)(C)O
t-butanol
CCN(CC)CC
triethylamine

Reagenzien

Keine

Lösungsmittel

C1COCCO1
dioxane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe solvents is removed under vacuum
  2. 2
    workup.DISSOLUTIONThe residue is dissolved in methylene chloride
  3. 3
    Waschenwashed with water
  4. 4
    Trocknendried over MgSO4
  5. 5
    Einengenconcentrated under vacuum
  6. 6
    SonstigeThe title compound is purified by chromatography on silica gel

Vorschrift

A sample of the product from Step 477d is heated with diphenylphosphoryl azide, t-butanol, triethylamine and dioxane. The solvents is removed under vacuum. The residue is dissolved in methylene chloride, washed with water and dried over MgSO4 and concentrated under vacuum. The title compound is purified by chromatography on silica gel.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05726182uspto-grants-1998_03