tert-Butanol → HCID 23159792, compound

HRID 1011430Notes

Reaction equation

HRID 1011430 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6](C(O)=O)[CH:7]=[N:8]2.CC[N:18]([CH2:21]C)CC.N(P(=O)(OC1C=CC=CC=1)[O:27]C1C=CC=CC=1)=[N+]=[N-].[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[C:42]([O:46][C:21]([NH:18][C:6]1[CH:7]=[N:8][C:9]2[C:4]([CH:5]=1)=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][CH:10]=2)=[O:27])([CH3:45])([CH3:44])[CH3:43]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 123414Diphenylphosphoryl azideHCID 231597415-Methoxyquinoline-3-carboxylic acid

Product 1

HCID 23159792HCID 23159792, compound

Procedure

To a solution of 5-methoxy-3-quinolinecarboxylic acid (2 g, 10 mmol) prepared in stage A of example 9 in tert-BuOH (15 mL) was added NEt3 (1.2 g, 12 mmol) and diphenyl azidophosphonate (DPPA) (2.1 mL, 10 mmol). The reaction mixture is refluxed for 24 hours. The solvent is evaporated under vacuum and the residue is dissolved in AcOEt (50 mL) and washed with a saturated NaHCO3 solution. After drying, the solvent is evaporated under vacuum affording the title compound.

Workup

  1. temperatureThe reaction mixture is refluxed for 24 hours
  2. customThe solvent is evaporated under vacuum
  3. dissolutionthe residue is dissolved in AcOEt (50 mL)
  4. washwashed with a saturated NaHCO3 solution
  5. customAfter drying
  6. customthe solvent is evaporated under vacuum

Sources & evidence

ORD record
ord-508f4deec15345079de4055d83592843
Source dataset
uspto-grants-2011_07
Patent number
US07977354B2

Reaction notes

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