tert-Butanol → 1-cyclopropyl-8-(1-Bocamino-1-cyclopropyl)-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester

HRID 1900

Reaction equation

HRID 1900 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[N:14]2[C:9]([C:10]([CH3:24])=[C:11]([C:18]3(C(O)=O)[CH2:20][CH2:19]3)[C:12]([F:17])=[CH:13]2)=[C:8]([CH:25]2[CH2:27][CH2:26]2)[CH:7]=1)=[O:5])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1.[C:45]([OH:49])([CH3:48])([CH3:47])[CH3:46].C([N:52]([CH2:55]C)CC)C>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[N:14]2[C:9]([C:10]([CH3:24])=[C:11]([C:18]3([NH:52][C:55]([O:49][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:35])[CH2:19][CH2:20]3)[C:12]([F:17])=[CH:13]2)=[C:8]([CH:25]2[CH2:26][CH2:27]2)[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 571289751-cyclopropyl-8-(1-hydroxycarbonyl-1-cyclopropyl)-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester

Product 1

HCID 571023201-cyclopropyl-8-(1-Bocamino-1-cyclopropyl)-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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.

Workup

  1. customThe solvents is removed under vacuum
  2. dissolutionThe residue is dissolved in methylene chloride
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customThe title compound is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-e9a35b5778f84e018ef46a7daf51dbfd
Source dataset
uspto-grants-1998_03
Patent number
US05726182

Linked notes

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