Potassium Hydroxide → 4,5-Difluoro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid

HRID 1047951Notes

Reaction equation

HRID 1047951 reaction equation
C([O:3][C:4]([C:6]1([NH:17][C:18](=[O:30])[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=2[CH:26]=[C:27]([CH3:29])[CH3:28])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([F:16])[C:12]=2[F:15])[CH2:7]1)=[O:5])C.[OH-].[K+]>CCO.O>[F:15][C:12]1[C:11]([F:16])=[CH:10][CH:9]=[C:8]2[C:13]=1[CH2:14][C:6]([NH:17][C:18](=[O:30])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:20]=1[CH:26]=[C:27]([CH3:28])[CH3:29])([C:4]([OH:5])=[O:3])[CH2:7]2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 59314094HCID 59314094, compound

Product 1

HCID 251028044,5-Difluoro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4,5-Difluoro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester (387) (650 mg, 1.57 mmol) is dissolved in EtOH (50 mL) and set to stir at RT. To this solution is added 5M KOH (4 mL). The reaction mixture is stirred at RT overnight. After concentration in vacuo, the residue obtained is dissolved in water (20 mL) and washed with EtOAc (20 mL). The phases are separated and the aqueous phase is acidified with concentrated HCl to pH 2. The solid precipitate is collected via filtration, dried under vacuum, and then purified on an HPLC. The desired product (388) is obtained as white solid (440.0 mg, 73%).

Workup

  1. stirringThe reaction mixture is stirred at RT overnight
  2. concentrationAfter concentration in vacuo
  3. customthe residue obtained
  4. washwashed with EtOAc (20 mL)
  5. customThe phases are separated
  6. filtrationThe solid precipitate is collected via filtration
  7. customdried under vacuum
  8. custompurified on an HPLC

Sources & evidence

ORD record
ord-9d7774112b134f1b8d1d781342dad818
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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