Potassium Hydroxide → HCID 59314378, compound

HRID 1047882Notes

Reaction equation

HRID 1047882 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:29])[CH:17]([CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[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>[CH:24]1([CH:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16]([NH:15][C:6]2([C:4]([OH:5])=[O:3])[CH2:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:14]2)=[O:29])[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59314123HCID 59314123, compound

Product 1

HCID 59314378HCID 59314378, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-Cyclopentyl-2-phenyl-acetylamino)-indan-2-carboxylic acid ethyl ester (268) (1 g, 2.56 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 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 and dried under vacuum. The desired product (269) is obtained as white solid (710 mg, 71%).

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. washwashed with EtOAc (20 ml)
  5. customThe phases are separated
  6. filtrationThe solid precipitate is collected via filtration
  7. customdried under vacuum

Sources & evidence

ORD record
ord-db0e40dbf43d49168663706da055a48d
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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