Reaction #1996

ord-e9a35b5778f84e018ef46a7daf51dbfd

Reaction equation

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

Reactants

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

Reagents

None

Solvents

C1COCCO1
dioxane

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

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

Procedure

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.v1Patent: US05726182uspto-grants-1998_03