Water → 5-(2-Isopropoxy-3-methyl-benzoylamino)-1,3-dimethyl-5,6-dihydro-4H-cyclopenta[c]thiophene-5-carboxylic acid

HRID 1047743Notes

Reaction equation

HRID 1047743 reaction equation
C([O:3][C:4]([C:6]1([NH:16][C:17](=[O:29])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=2[O:25][CH:26]([CH3:28])[CH3:27])[CH2:15][C:9]2=[C:10]([CH3:14])[S:11][C:12]([CH3:13])=[C:8]2[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[CH:26]([O:25][C:19]1[C:20]([CH3:24])=[CH:21][CH:22]=[CH:23][C:18]=1[C:17]([NH:16][C:6]1([C:4]([OH:5])=[O:3])[CH2:7][C:8]2=[C:12]([CH3:13])[S:11][C:10]([CH3:14])=[C:9]2[CH2:15]1)=[O:29])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 59314177HCID 59314177, compound

Product 1

HCID 593144135-(2-Isopropoxy-3-methyl-benzoylamino)-1,3-dimethyl-5,6-dihydro-4H-cyclopenta[c]thiophene-5-carboxylic acidYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 5-(2-isopropoxy-3-methyl-benzoylamino)-1,3-dimethyl-5,6-dihydro-4H-cyclopenta[c]thiophene-5-carboxylic acid ethyl ester (88) (448 mg, 1.08 mmol) and KOH (1 g, 18 mmol) is dissolved in EtOH (8 mL) and water (1 mL) under a water bath. The water bath is removed when KOH is completely dissolved and the resulting reaction solution is stirred at RT for 8 h. After concentration in vacuo, the residue is dissolved in water (20 mL) and acidified with conc. HCl until no more precipitate formed. The precipitate is filtered to give a pure product (89) as a brown solid (360 mg, 86%).

Workup

  1. customThe water bath is removed when KOH
  2. dissolutionis completely dissolved
  3. customthe resulting reaction solution
  4. concentrationAfter concentration in vacuo
  5. dissolutionthe residue is dissolved in water (20 mL)
  6. customformed
  7. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-2409a7af1bee418aba4a60671acaca4c
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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