Water → HCID 25160413, compound

HRID 1047755Notes

Reaction equation

HRID 1047755 reaction equation
C([O:3][C:4]([C:6]1([NH:17][C:18](=[O:31])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=2[O:26][CH:27]2[CH2:30][CH2:29][CH2:28]2)[CH2:14][C:13]2[C:8](=[CH:9][C:10]([F:16])=[C:11]([F:15])[CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[CH:27]1([O:26][C:20]2[C:21]([CH3:25])=[CH:22][CH:23]=[CH:24][C:19]=2[C:18]([NH:17][C:6]2([C:4]([OH:5])=[O:3])[CH2:7][C:8]3[C:13](=[CH:12][C:11]([F:15])=[C:10]([F:16])[CH:9]=3)[CH2:14]2)=[O:31])[CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 59314183Ethyl 2-[[2-(cyclobutyloxy)-3-methylbenzoyl]amino]-5,6-difluoro-2,3-dihydro-1H-indene-2-carboxylate

Product 1

HCID 25160413HCID 25160413, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture 2-(2-cyclobutoxy-3-methyl-benzoylamino)-5,6-difluoro-indan-2-carboxylic acid ethyl ester (104) (367 mg, 0.85 mmol) and KOH (600 mg, 10.7 mmol) is dissolved in EtOH (10 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 (30 mL) and acidified with conc. HCl until no more white precipitate formed. After the filtration, the solid is purified by HPLC to give a pure product (105) as white solid (300 mg, 88%).

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 (30 mL)
  6. customformed
  7. filtrationAfter the filtration
  8. customthe solid is purified by HPLC

Sources & evidence

ORD record
ord-6c678c808826468294e21126a075acbc
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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