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

HRID 2037181Notes

Reaction equation

HRID 2037181 reaction equation
[C:1]([C:5]1[C:6]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH2:20][C:21]([O:23]C)=[O:22])[N:11]([C:25]3[CH:30]=[CH:29][C:28]([C:31]4[CH:35]=[CH:34][S:33][CH:32]=4)=[CH:27][CH:26]=3)[C:10](=[O:36])[C:7]=2NN=1)([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-:42].[Li+].Cl.[OH2:45]>CO>[OH:23][C:21]([CH2:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[CH:12]1[N:11]([C:25]2[CH:26]=[CH:27][C:28]([C:31]3[CH:35]=[CH:34][S:33][CH:32]=3)=[CH:29][CH:30]=2)[C:10](=[O:36])[C:7]([OH:42])=[C:6]1[C:5](=[O:45])[C:1]([CH3:4])([CH3:3])[CH3:2])=[O:22]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 178501755HCID 178501755, compound

Product 1

HCID 583657045-(2-Hydroxycarbonylmethyloxyphenyl)-4-(2,2-dimethylpropionyl)-3-hydroxy-1-(4-thiophene-3-ylphenyl)-1,5-dihydropyrrole-2-oneYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 3-t-butyl-5-(4-thiophene-3-ylphenyl)-4-(2-methoxycarbonylmethyloxyphenyl)-4,5-dihydro-1H-pyrrolo[3,4-c]pyrazole-6-one (0.124 g, 0.25 mmol), THF (1.24 mL) and methanol (1.24 mL) was added 1 mol/L aqueous lithium hydroxide solution (0.74 mL), and the resulting mixture was stirred at room temperature for 1.5 hours. After the reaction was completed, 2 mol/L hydrochloric acid (0.38 mL) and water (10 mL) were poured into the reaction mixture, and the precipitated aimed compound was collected by filtration. The resulting aimed compound was dissolved in ethyl acetate, and the solution 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 (0.104 g, yield: 87%) as pale brown 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 solution 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-bab4301defac495c9d51e9f53682e86a
Source dataset
uspto-grants-2013_11
Patent number
US08575197B2

Reaction notes

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