Water → HCID 25160280, compound

HRID 1047678Notes

Reaction equation

HRID 1047678 reaction equation
C([O:3][C:4]([C:6]1([NH:16][C:17](=[O:31])[C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20]([Cl:25])[C:19]=2[O:26][CH:27]2[CH2:30][CH2:29][CH2:28]2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:15])[CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[Cl:25][C:20]1[C:19]([O:26][CH:27]2[CH2:30][CH2:29][CH2:28]2)=[C:18]([CH:23]=[C:22]([Cl:24])[CH:21]=1)[C:17]([NH:16][C:6]1([C:4]([OH:5])=[O:3])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:15])[CH:12]=2)[CH2:7]1)=[O:31]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 59314158HCID 59314158, compound

Product 1

HCID 25160280HCID 25160280, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 2-(3,5-dichloro-2-cyclobutoxy-benzoylamino)-5-fluoro-indan-2-carboxylic acid ethyl ester (20) (300 mg, 0.64 mmol) and KOH (500 mg, 8.9 mmol) is dissolved in EtOH (5 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 6 h. After concentration in vacuo, the residue is dissolved in water (20 mL) and acidified with conc. HCl until pH˜3. The precipitate is filtered to give a pure product (21) as white solid (200 mg, 71%).

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. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-baf58772a6fb4a93a0ba2885dde2e7c9
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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