Potassium Hydroxide → HCID 25161049, compound

HRID 1047880Notes

Reaction equation

HRID 1047880 reaction equation
C([O:3][C:4]([C:6]1([NH:16][C:17](=[O:30])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:19]=2[O:25][CH:26]2[CH2:29][CH2:28][CH2:27]2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[F:15])[CH2:7]1)=[O:5])C.[OH-].[K+]>CCO>[CH:26]1([O:25][C:19]2[C:20]([CH3:24])=[CH:21][CH:22]=[CH:23][C:18]=2[C:17]([NH:16][C:6]2([C:4]([OH:5])=[O:3])[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][C:12]=3[F:15])[CH2:7]2)=[O:30])[CH2:27][CH2:28][CH2:29]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59314196HCID 59314196, compound

Product 1

HCID 25161049HCID 25161049, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-Cyclobutoxy-3-methyl-benzoylamino)-4-fluoro-indan-2-carboxylic acid ethyl ester (7) (210 mg, 0.51 mmol) is dissolved in EtOH (50 mL) and set to stir at RT. To this solution is added 5M KOH (3 ml). The reaction mixture is stirred at RT overnight. After concentration in vacuo, the residue is dissolved in water (20 mL) and acidified with concentrated HCl to pH 2. The resultant mixture is washed with EtOAc (3×100 ml). Organics are combined and washed with brine, then dried over anhydrous Na2SO4 and concentrated in vacuo. The desired product (267) is obtained as white solid (168 mg, 86%).

Workup

  1. stirringThe reaction mixture is stirred at RT overnight
  2. concentrationAfter concentration in vacuo
  3. dissolutionthe residue is dissolved in water (20 mL)
  4. washThe resultant mixture is washed with EtOAc (3×100 ml)
  5. washwashed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-811e1df8f89c40278b7990438eb6e944
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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