Sodium Hydroxide → HCID 21310921, compound

HRID 583300Notes

Reaction equation

HRID 583300 reaction equation
C[O:2][C:3](=[O:31])[C:4]1[CH:9]=[C:8]([Br:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[N:12]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14].[OH-].[Na+]>CO.C1COCC1>[CH2:24]([N:12]([S:13]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)(=[O:15])=[O:14])[C:5]1[C:6]([CH3:11])=[CH:7][C:8]([Br:10])=[CH:9][C:4]=1[C:3]([OH:31])=[O:2])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 70052828HCID 70052828, compound

Product 1

HCID 21310921HCID 21310921, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 0.444 g (0.88 lmmol) of the product of Example 11 in 20 mL of MeOH/THF (1:1) was added 9.3 mL 1N NaOH and the mixture heated at reflux for 18 h. The mixture was cooled to room temperature and the organic removed in vacuo. The remaining solution was acidified with 10% HCl and extracted with EtOAc. The extract was washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue provided 0.364 g (84%) of the desired carboxylic acid as a white solid after trturation with ether. CI Mass Spec: 490 (M+H).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 18 h
  3. customthe organic removed in vacuo
  4. extractionextracted with EtOAc
  5. washThe extract was washed with water and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c014fcc1c49d4b90ab818959e4ec50d5
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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