Sodium Hydroxide → HCID 54012975, compound

HRID 2187392Notes

Reaction equation

HRID 2187392 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH:5](C(OCC)=O)[CH:6]([C:14]1[CH:15]=[N:16][C:17]([CH3:20])=[N:18][CH:19]=1)[CH2:7][C:8](=[O:13])[CH2:9][CH2:10][CH:11]=[CH2:12])[CH3:2].[OH-].[Na+]>CCO>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][CH:6]([C:14]1[CH:15]=[N:16][C:17]([CH3:20])=[N:18][CH:19]=1)[CH2:7][C:8](=[O:13])[CH2:9][CH2:10][CH:11]=[CH2:12])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70094731HCID 70094731, compound

Product 1

HCID 54012975HCID 54012975, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

The diester 15-4 (11.2 g, 31.1 mmol) was dissolved in EtOH (100 mL) at room temperature. To this was added 1N NaOH (31.1 mL, 31.1 mmol), the mixture stirred at 40° C. for 2 hours then overnight at room temperature. The mixture was concentrated in vacuo, dissolved in toluene (100 mL) and heated at reflux for 5 hours. After removal of the solvent, the residue was partitioned between water and CHCl3 washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (eluting with EtOAc) to give the ester 15-5 as an oil.

Workup

  1. customovernight
  2. customat room temperature
  3. concentrationThe mixture was concentrated in vacuo
  4. dissolutiondissolved in toluene (100 mL)
  5. temperatureheated
  6. temperatureat reflux for 5 hours
  7. customAfter removal of the solvent
  8. customthe residue was partitioned between water and CHCl3
  9. washwashed with brine
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by silica gel chromatography (eluting with EtOAc)

Sources & evidence

ORD record
ord-94ef4283da3c48aebaed40e8eb9bebfb
Source dataset
uspto-grants-2002_06
Patent number
US06410526B1

Reaction notes

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