Potassium Hydroxide → 2-[2-(2-Methyl-propenyl)-3-trifluoromethyl-benzoylamino]-indan-2-carboxylic acid

HRID 1047960Notes

Reaction equation

HRID 1047960 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:31])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]([F:26])([F:25])[F:24])[C:18]=2[CH:27]=[C:28]([CH3:30])[CH3:29])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+]>CCO>[CH3:29][C:28]([CH3:30])=[CH:27][C:18]1[C:19]([C:23]([F:24])([F:25])[F:26])=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]([NH:15][C:6]1([C:4]([OH:5])=[O:3])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:31]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 685910012-[2-(2-Methyl-propenyl)-3-trifluoromethyl-benzoylamino]-indan-2-carboxylic acid ethyl ester

Product 1

HCID 685886202-[2-(2-Methyl-propenyl)-3-trifluoromethyl-benzoylamino]-indan-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[2-(2-Methyl-propenyl)-3-trifluoromethyl-benzoylamino]-indan-2-carboxylic acid ethyl ester (2) (100 mg, 0.32 mmol) is dissolved in EtOH (20 mL) and set to stir at RT. To this solution is added 5M KOH (2 mL). The reaction mixture is heated to reflux and stirred for 1 h. After concentration in vacuo, the resulting residue is dissolved in water (10 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 50 mL ether (3×). Organic phases are collected, concentrated to dryness, then the resulting residue is purified on an HPLC. The desired product (397) is obtained as white solid (40.0 mg, 43%).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux
  3. stirringstirred for 1 h
  4. concentrationAfter concentration in vacuo
  5. dissolutionthe resulting residue is dissolved in water (10 mL)
  6. washwashed with EtOAc (20 mL)
  7. customThe phases are separated
  8. washThe aqueous phase is washed with 50 mL ether (3×)
  9. customOrganic phases are collected
  10. concentrationconcentrated to dryness
  11. customthe resulting residue is purified on an HPLC

Sources & evidence

ORD record
ord-10d289d84d3b44a5952afc0aaa26787c
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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