Reacción #1996

ord-e9a35b5778f84e018ef46a7daf51dbfd

Ecuación de reacción

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

Reactantes

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

Reactivos

Ninguno

Disolventes

C1COCCO1
dioxane

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe solvents is removed under vacuum
  2. 2
    workup.DISSOLUTIONThe residue is dissolved in methylene chloride
  3. 3
    Lavadowashed with water
  4. 4
    Secadodried over MgSO4
  5. 5
    Concentraciónconcentrated under vacuum
  6. 6
    OtroThe title compound is purified by chromatography on silica gel

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05726182uspto-grants-1998_03