Réaction #1996

ord-e9a35b5778f84e018ef46a7daf51dbfd

Équation de réaction

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

Réactifs

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

Réactifs

Aucun

Solvants

C1COCCO1
dioxane

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe solvents is removed under vacuum
  2. 2
    workup.DISSOLUTIONThe residue is dissolved in methylene chloride
  3. 3
    Lavagewashed with water
  4. 4
    Séchagedried over MgSO4
  5. 5
    Concentrationconcentrated under vacuum
  6. 6
    AutreThe title compound is purified by chromatography on silica gel

Mode opératoire

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05726182uspto-grants-1998_03