Potassium Hydroxide → 4,7-Difluoro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid

HRID 1047956Notes

Reaction equation

HRID 1047956 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](=[C:9]([F:16])[CH:10]=[CH:11][C:12]=2[F:15])[CH2:7]1)=[O:5])C.[OH-].[K+]>CCO.O>[F:15][C:12]1[CH:11]=[CH:10][C:9]([F:16])=[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 593143184,7-Difluoro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester

Product 1

HCID 251612984,7-Difluoro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4,7-Difluoro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester (391) (133 mg, 0.32 mmol) is dissolved in EtOH (20 mL) and set to stir at RT. To this solution was added 5M KOH (2 ml). The reaction mixture was stirred at RT. 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 aqueous phase is washed with 100 mL EtOAc. The organic phases were collected, concentrated to dryness, and then the resulting residue is purified on an HPLC. The desired product (392) is obtained as white solid (38 mg, 28%).

Workup

  1. stirringThe reaction mixture was stirred at RT
  2. concentrationAfter concentration in vacuo
  3. customthe residue obtained
  4. washwashed with EtOAc (20 mL)
  5. customThe phases are separated
  6. washThe aqueous phase is washed with 100 mL EtOAc
  7. customThe organic phases were collected
  8. concentrationconcentrated to dryness
  9. customthe resulting residue is purified on an HPLC

Sources & evidence

ORD record
ord-258d59b756174a8dbf3277a66e7afbbc
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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