Sodium Hydroxide → HCID 21310920, compound

HRID 583301Notes

Reaction equation

HRID 583301 reaction equation
C([O:8][C:9](=[O:36])[C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]=1[N:17]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])C1C=CC=CC=1.[OH-].[Na+]>CO>[CH2:29]([N:17]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[C:11]1[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:10]=1[C:9]([OH:36])=[O:8])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 15859209HCID 15859209, compound

Product 1

HCID 21310920HCID 21310920, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product of Example 12 in 30 mL of methanol was added 7.5 mL (0.038 mol) of 5N sodium hydroxide solution and the resulting mixture was heated to reflux for 66 h. The reaction was then cooled to room tempeature 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 0.984 g (79%) of the desired carboxylic acid as a white solid. Electospray Mass Spec: 427 (M+H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 66 h
  3. temperatureThe reaction was then cooled to room tempeature
  4. customthe organics were removed in vacuo
  5. extractionextracted with EtOAc
  6. washThe combined organics were washed with water and brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting residue was triturated with ether
  11. filtrationfiltered

Sources & evidence

ORD record
ord-764c4c758b1441d79337e8d38fb44cd2
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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