Oxalic Acid → (2R)-1-(3'-(Methoxycarbonyl)biphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol oxalic acid salt

HRID 1600967Notes

Reaction equation

HRID 1600967 reaction equation
S(=O)(=O)(O)O.[C:6]([C:9]1[CH:10]=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@H:23]([OH:32])[CH2:24][CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:17][CH:16]=2)[CH:12]=[CH:13][CH:14]=1)([OH:8])=[O:7].[C:33](=O)([O-])O.[Na+].[C:38]([OH:43])(=[O:42])[C:39]([OH:41])=[O:40]>CO.CCOCC>[C:38]([OH:43])(=[O:42])[C:39]([OH:41])=[O:40].[CH3:33][O:7][C:6]([C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:22][C@H:23]([OH:32])[CH2:24][CH2:25][C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)=[CH:19][CH:20]=2)[CH:12]=[CH:13][CH:14]=1)=[O:8]

Participants

7

Reactant 4

HCID 971Oxalic AcidHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 54073875(2R)-1-(3'-Carboxybiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

Product 1

HCID 67597801(2R)-1-(3'-(Methoxycarbonyl)biphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol oxalic acid salt

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

Concentrated sulfuric acid (2.5 ml) was added to a suspension of (2R)-1-(3'-carboxybiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol (0.5 g) in methanol (50 ml). The mixture was heated at reflux for 10 hours. The mixture was cooled to room temperature and made basic by addition of aqueous sodium hydrogen carbonate. The mixture was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with dichloromethane:methanol (19:1) to give an oil which was converted to the oxalate salt upon treatment with oxalic acid (excess) in ether to give the title compound as a solid (0.482 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 10 hours
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography over silica eluting with dichloromethane:methanol (19:1)
  8. customto give an oil which

Sources & evidence

ORD record
ord-32e69279272a4c80baf9bc4bca78ad28
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

Loading…