Sodium Hydroxide → HCID 21310862, compound

HRID 583325Notes

Reaction equation

HRID 583325 reaction equation
C[O:2][C:3](=[O:33])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[N:12]([S:22]([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)(=[O:24])=[O:23])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=1.[OH-].[Na+]>CO.C1COCC1>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([S:22]([N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[CH:15]=2)[C:5]2[C:6]([CH3:11])=[CH:7][C:8]([CH3:10])=[CH:9][C:4]=2[C:3]([OH:33])=[O:2])(=[O:24])=[O:23])=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 70055700HCID 70055700, compound

Product 1

HCID 21310862HCID 21310862, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.610 g (1.3 mmol) of the product of Example 103 in 6.5 mL methanol and 6.5 mL of THF was added 6.5 mL of 1N NaOH solution. The reaction mixture was refluxed for 18 hr and the organics were removed in vacuo. The resulting mixture was diluted with water, acidified with 3N 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 0.417 g (79%) of the desired carboxylic acid as a white solid. Electrospray Mass Spec 456.3(M+H).

Workup

  1. temperatureThe reaction mixture was refluxed for 18 hr
  2. customthe organics were removed in vacuo
  3. additionThe resulting mixture was diluted with water
  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-8ee46ce8fdab4f3588a8289bc4db1d34
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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