Potassium Hydroxide → HCID 25161302, compound

HRID 1047958Notes

Reaction equation

HRID 1047958 reaction equation
C([O:3][C:4]([C:6]1([NH:16][C:17](=[O:29])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=2[CH:25]=[C:26]([CH3:28])[CH3:27])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:15])[CH:12]=2)[CH2:7]1)=[O:5])C.[OH-].[K+]>CCO>[Cl:15][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]([NH:16][C:17](=[O:29])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=1[CH:25]=[C:26]([CH3:27])[CH3:28])([C:4]([OH:5])=[O:3])[CH2:14]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59314096HCID 59314096, compound

Product 1

HCID 25161302HCID 25161302, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Chloro-2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid ethyl ester (394) (120 mg, 0.3 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 stirred at RT overnight. After concentration in vacuo, the resulting residue 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 are collected, concentrated to dryness, and then the resulting residue is purified on an HPLC. The desired product (395) is obtained as white solid (73 mg, 63%).

Workup

  1. stirringThe reaction mixture is stirred at RT overnight
  2. concentrationAfter concentration in vacuo
  3. dissolutionthe resulting residue is dissolved in water (20 mL)
  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 are collected
  8. concentrationconcentrated to dryness
  9. customthe resulting residue is purified on an HPLC

Sources & evidence

ORD record
ord-13b24c66ca804172a2fc6709af858bec
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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