Potassium Carbonate → HCID 58679074, compound

HRID 1442533Notes

Reaction equation

HRID 1442533 reaction equation
C([O:4][CH2:5][CH2:6][N:7]1[C:11]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=2[OH:19])=[C:10]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:9]2[S:26][C:27]([C:29]([O:31][CH3:32])=[O:30])=[CH:28][C:8]1=2)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[CH:20]1([C:10]2[C:9]3[S:26][C:27]([C:29]([O:31][CH3:32])=[O:30])=[CH:28][C:8]=3[N:7]([CH2:6][CH2:5][OH:4])[C:11]=2[C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=2[OH:19])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58679100HCID 58679100, compound

Product 1

HCID 58679074HCID 58679074, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-(2-acetoxyethyl)-6-cyclohexyl-5-(2,4-dihydroxyphenyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate (505 mg, 1.11 mmol) in methanol (5 ml) was added potassium carbonate (476 mg, 3.44 mmol) and the mixture was stirred at room temperature for 25 min. The reaction mixture was concentration under reduced pressure, and ethyl acetate (5 ml) was added to the residue. The organic layer was washed successively with 1N hydrochloric acid (4 ml) and saturated brine (5 ml×2), and dried over sodium sulfate. Filtration and concentration gave methyl 6-cyclohexyl-5-(2,4-dihydroxyphenyl)-4-(2-hydroxyethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate as a crude product. The obtained compound was used for Step 11 without further purification.

Workup

  1. concentrationconcentration under reduced pressure, and ethyl acetate (5 ml)
  2. additionwas added to the residue
  3. washThe organic layer was washed successively with 1N hydrochloric acid (4 ml) and saturated brine (5 ml×2)
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-624e92e92a244b31b53fe54f76077af5
Source dataset
uspto-grants-2010_02
Patent number
US07659263B2

Reaction notes

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