Hydrochloric Acid → 146939-64-2

HRID 1956757Notes

Reaction equation

HRID 1956757 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]([O:15][C:16]2[CH:39]=[CH:38][C:19]([C:20]([C:22]3[CH:23]=[C:24]([CH2:31][CH2:32][CH2:33][C:34]([O:36]C)=[O:35])[N:25]4[C:30]=3[CH:29]=[CH:28][CH:27]=[CH:26]4)=[O:21])=[CH:18][CH:17]=2)[CH2:12][CH2:13][CH3:14])=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[OH-].[Na+].C(OCC)(=O)C.Cl>C(O)C>[CH2:1]([C:5]1[CH:6]=[CH:7][C:8]([C@@H:11]([O:15][C:16]2[CH:17]=[CH:18][C:19]([C:20]([C:22]3[CH:23]=[C:24]([CH2:31][CH2:32][CH2:33][C:34]([OH:36])=[O:35])[N:25]4[C:30]=3[CH:29]=[CH:28][CH:27]=[CH:26]4)=[O:21])=[CH:38][CH:39]=2)[CH2:12][CH2:13][CH3:14])=[CH:9][CH:10]=1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 18663760methyl 4-[1-[4-[1-(S)-(4-isobutylphenyl)butoxy]benzoyl]indolizin-3-yl]butyrate

Product 1

HCID 9892592146939-64-2Yield 50.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 4-[1-[4-[1-(S)-(4-isobutylphenyl)butoxy]benzoyl]indolizin-3-yl]butyrate (182 mg) in ethanol (4 ml) was added 1N aqueous solution of sodium hydroxide (0.6 ml). The mixture was stirred at 50° C. for 40 minutes, and then poured into a mixture of ethyl acetate and diluted hydrochloric acid. The organic layer was separated, washed with water, dried over magnesium sulfate and evaporated. The residue was crystallized with diisopropyl ether to give 4-[l-[4-[l-(S)-(4-isobutylphenyl)butoxy]benzoyl]indolizin-3-yl]butyric acid as white powder (89 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue was crystallized with diisopropyl ether

Sources & evidence

ORD record
ord-5f661f7ad0774c4d8bc66fd015006768
Source dataset
uspto-grants-1998_07
Patent number
US05780633

Reaction notes

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