Sodium Hydroxide → HCID 21251112, compound

HRID 1275638Notes

Reaction equation

HRID 1275638 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:30])[C:10]=1[N:11]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)(=[O:14])=[O:13])=[O:5])C.[OH-].[Na+]>C1COCC1>[CH2:23]([N:11]([S:12]([C:15]1[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=1)(=[O:14])=[O:13])[C:10]1[N:9]([CH3:30])[N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54425806HCID 54425806, compound

Product 1

HCID 21251112HCID 21251112, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.799 g (1.862 mmol) of the product of Example 7 in 20 mL of methano/THF (1:1) was added 9.3 mL of 1N sodium hydroxide solution and the resulting mixture was heated to reflux for 18 h. The reaction was then cooled to room temperature and the organics were removed in vacuo. The resulting mixture was acidified with 10% HCl and extracted with EtOAc. The combined organics were washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was triturated with ether and filtered to provide 0.697 g (93%) of the desired carboxylic acid as a white solid. Electrospray Mass Spec: 402 (M+H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 18 h
  3. customthe organics were removed in vacuo
  4. extractionextracted with EtOAc
  5. washThe combined organics were washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting residue was triturated with ether
  10. filtrationfiltered

Sources & evidence

ORD record
ord-2e574fe9b8c54062b19e874fc4e2a25c
Source dataset
uspto-grants-2000_12
Patent number
US06162821

Reaction notes

Loading…