Hydrochloric Acid → 5-(2-Hydroxycarbonylmethyloxyphenyl)-4-(2,2-dimethylpropionyl)-3-hydroxy-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one

HRID 2037179Notes

Reaction equation

HRID 2037179 reaction equation
[CH3:1][C:2]([CH3:36])([CH3:35])[C:3]([C:5]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH2:17][C:18]([O:20]C)=[O:19])[N:8]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:32]=[CH:31][S:30][CH:29]=3)=[CH:24][CH:23]=2)[C:7](=[O:33])[C:6]=1[OH:34])=[O:4].C1COCC1.[OH-].[Li+].Cl>O.CO>[OH:20][C:18]([CH2:17][O:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[CH:9]1[N:8]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:32]=[CH:31][S:30][CH:29]=3)=[CH:24][CH:23]=2)[C:7](=[O:33])[C:6]([OH:34])=[C:5]1[C:3](=[O:4])[C:2]([CH3:35])([CH3:1])[CH3:36])=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 583653294-(2,2-Dimethylpropionyl)-3-hydroxy-5-(2-methoxycarbonylmethyloxyphenyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one

Product 1

HCID 583657045-(2-Hydroxycarbonylmethyloxyphenyl)-4-(2,2-dimethylpropionyl)-3-hydroxy-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-oneYield 82%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 4-(2,2-dimethylpropionyl)-3-hydroxy-5-(2-methoxycarbonylmethyloxyphenyl)-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one (0.172 g, 0.34 mmol), THF (1.72 mL), and methanol (1.72 mL) was added 1 mol/L aqueous lithium hydroxide solution (1.02 mL), and the resulting mixture was stirred at room temperature for 1 hour. After the reaction was completed, 2 mol/L hydrochloric acid (0.52 mL) and water (14 mL) were added to the reaction mixture, and the precipitated aimed compound was collected by filtration. The resulting aimed compound was dissolved in ethyl acetate, and the mixture was dried over anhydrous sodium sulphate and then concentrated in vacuo. The resulting residue was triturated with ethyl ether and diisopropyl ether to give 5-(2-hydroxycarbonylmethyloxyphenyl)-4-(2,2-dimethylpropionyl)-3-hydroxy-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-one (0.137 g, yield: 82%) as pale yellow solid.

Workup

  1. customthe precipitated aimed compound
  2. filtrationwas collected by filtration
  3. dissolutionThe resulting aimed compound was dissolved in ethyl acetate
  4. dry with materialthe mixture was dried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was triturated with ethyl ether and diisopropyl ether

Sources & evidence

ORD record
ord-3b534549d7f545a1a363ae60920636cf
Source dataset
uspto-grants-2013_11
Patent number
US08575197B2

Reaction notes

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