Sodium Hydroxide → HCID 22924079, compound

HRID 2258027Notes

Reaction equation

HRID 2258027 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:33]3[CH:41]=[CH:40][C:36]4[O:37][CH2:38][O:39][C:35]=4[CH:34]=3)[CH:11]([NH:17][C:18](=[O:32])[CH:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:12]([O:14]CC)=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1.[OH-].[Na+]>CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:33]3[CH:41]=[CH:40][C:36]4[O:37][CH2:38][O:39][C:35]=4[CH:34]=3)[CH:11]([NH:17][C:18](=[O:32])[CH:19]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:12]([OH:14])=[O:13])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 131720124HCID 131720124, compound

Product 1

HCID 22924079HCID 22924079, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ester of Example 20 (0.470 g, 0.85 mmol) is dissolved in 100 mL of methanol. The solution is treated with 4.5 mL of 1N aqueous sodium hydroxide and stirred under reflux for 6 hours. Another 4.5 mL of 1N sodium hydroxide is added and reflux is continued for 24 hours. The methanol is evaporated in vacuo and the residue is dissolved in water. The solution is washed with ether, acidified with 3N hydrochloric acid and extracted with ethyl acetate (3×50 mL). The organic phase is dried (magnesium sulfate), filtered, and evaporated to give 0.407 g (91%) of product as a white solid;

Workup

  1. temperatureunder reflux for 6 hours
  2. temperaturereflux
  3. customThe methanol is evaporated in vacuo
  4. dissolutionthe residue is dissolved in water
  5. washThe solution is washed with ether
  6. extractionextracted with ethyl acetate (3×50 mL)
  7. dry with materialThe organic phase is dried (magnesium sulfate)
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-0a4a0de5c9da4b92bfec6769d4b8cbb2
Source dataset
uspto-grants-1997_08
Patent number
US05658943

Reaction notes

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