Water → 2-(2-Cyclobutoxy-3-methyl-benzoylamino)-indan-2-carboxylic acid

HRID 1047666Notes

Reaction equation

HRID 1047666 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:29])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[O:24][CH:25]2[CH2:28][CH2:27][CH2:26]2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[CH:25]1([O:24][C:18]2[C:19]([CH3:23])=[CH:20][CH:21]=[CH:22][C:17]=2[C:16]([NH:15][C:6]2([C:4]([OH:5])=[O:3])[CH2:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:14]2)=[O:29])[CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 593140752-(2-Cyclobutoxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester

Product 1

HCID 251602822-(2-Cyclobutoxy-3-methyl-benzoylamino)-indan-2-carboxylic acidYield 81.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-(2-cyclobutoxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (8) (250 mg, 0.64 mmol) and KOH (600 mg, 10.7 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 the solution acidified with conc. HCl until pH˜3 to yield a precipitate. The precipitate is filtered to give a pure product (9) as white solid (190 mg, 81%).

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. customto yield a precipitate
  7. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-2b2eef3e90e2486caf9f060d096dab49
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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