Hydrochloric Acid → 3-[5-{[1-isopentyl-4-(3-methylbutanoyl)-1H-pyrrol-2-yl]carbonyl}-2-(isopentyloxy)phenyl]propanoic acid

HRID 2249656Notes

Reaction equation

HRID 2249656 reaction equation
[CH2:1]([N:6]1[CH:10]=[C:9]([C:11](=[O:16])[CH2:12][CH:13]([CH3:15])[CH3:14])[CH:8]=[C:7]1[C:17]([C:19]1[CH:20]=[CH:21][C:22]([O:35][CH2:36][CH2:37][CH:38]([CH3:40])[CH3:39])=[C:23]([CH2:25][CH2:26][C:27]([O:29]CCC(C)C)=[O:28])[CH:24]=1)=[O:18])[CH2:2][CH:3]([CH3:5])[CH3:4].[OH-].[Na+].O.Cl>C(O)C.C(Cl)(Cl)Cl>[CH2:1]([N:6]1[CH:10]=[C:9]([C:11](=[O:16])[CH2:12][CH:13]([CH3:15])[CH3:14])[CH:8]=[C:7]1[C:17]([C:19]1[CH:20]=[CH:21][C:22]([O:35][CH2:36][CH2:37][CH:38]([CH3:40])[CH3:39])=[C:23]([CH2:25][CH2:26][C:27]([OH:29])=[O:28])[CH:24]=1)=[O:18])[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68985376isopentyl 3-[5-{[1-isopentyl-4-(3-methylbutanoyl)-1H-pyrrol-2-yl]carbonyl}-2-(isopentyloxy)phenyl]propanoate

Product 1

HCID 576843813-[5-{[1-isopentyl-4-(3-methylbutanoyl)-1H-pyrrol-2-yl]carbonyl}-2-(isopentyloxy)phenyl]propanoic acidYield 95.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 0.67 g of isopentyl 3-[5-{[1-isopentyl-4-(3-methylbutanoyl)-1H-pyrrol-2-yl]carbonyl}-2-(isopentyloxy)phenyl]propanoate in 14 ml of ethanol is added 3.6 ml of 1 mol/L sodium hydroxide solution. The mixture thus obtained is stirred at 50° C. for one hour. Water and chloroform are added to the reaction mixture, pH is adjusted to 2 with 6 mol/L hydrochloric acid, and the organic layer is separated. The organic layer is washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure. Thus, 0.56 g of 3-[5-{[1-isopentyl-4-(3-methylbutanoyl)-1H-pyrrol-2-yl]carbonyl}-2-(isopentyloxy)phenyl]propanoic acid is obtained as a white solid product.

Workup

  1. customThe mixture thus obtained
  2. customthe organic layer is separated
  3. washThe organic layer is washed with water and saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-2ac770576048451a91238498c7e32575
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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