Hydrochloric Acid → HCID 19010740, compound

HRID 1741857Notes

Reaction equation

HRID 1741857 reaction equation
C([O:4][CH:5]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]([O:20][C:21]2[CH:45]=[CH:44][C:24]([C:25]([C:27]3[C:28](CCCC(OCC)=O)=[CH:29][N:30]4[C:35]=3[CH:34]=[CH:33][CH:32]=[CH:31]4)=[O:26])=[CH:23][CH:22]=2)[CH2:16][CH2:17][CH2:18][CH3:19])=[C:11]([F:46])[CH:10]=1)[CH:6]([CH3:8])[CH3:7])(=O)C.[OH-].[Na+].[C:49]([O:52]CC)(=[O:51])[CH3:50].Cl.[CH2:56](O)[CH3:57]>O1CCOCC1>[F:46][C:11]1[CH:10]=[C:9]([CH:5]([OH:4])[CH:6]([CH3:7])[CH3:8])[CH:14]=[CH:13][C:12]=1[CH:15]([O:20][C:21]1[CH:45]=[CH:44][C:24]([C:25]([C:27]2[CH:28]=[C:29]([CH2:56][CH2:57][CH2:50][C:49]([OH:52])=[O:51])[N:30]3[C:35]=2[CH:34]=[CH:33][CH:32]=[CH:31]3)=[O:26])=[CH:23][CH:22]=1)[CH2:16][CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 19010772HCID 19010772, compound

Product 1

HCID 19010740HCID 19010740, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 4-[1-[4-[1-[4-(1-acetoxy-2-methylpropyl)-2-fluorophenyl]pentyloxy]benzoyl]indolizin-yl]butyrate (300 mg) in ethanol (3 ml) and 1,4-dioxane (3 ml) was added 1N aqueous solution of sodium hydroxide (1.5 ml). The mixture was stirred at room temperature for 1 hour, and then poured into a mixture of ethyl acetate and 0.5N hydrochloric acid. The organic layer was separated, washed with water and brine, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel column eluting with a mixture of chloroform and methanol (25:1) to give 4-[1-[4-[1-[2-fluoro-4-(1-hydroxyl-2-methylpropyl)phenyl]-pentyloxy]benzoyl]indolizin-3-yl]butyric acid (151 mg) as powder.

Workup

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel column
  6. washeluting with a mixture of chloroform and methanol (25:1)

Sources & evidence

ORD record
ord-0f6e815b8f8445749b6164711f05cc85
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

Loading…