Water → HCID 25161050, compound

HRID 1047899Notes

Reaction equation

HRID 1047899 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][C:6]1([NH:15][C:16](=[O:29])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[O:24][CH:25]2[CH2:28][CH2:27][CH2:26]2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)C.O.[OH-].[Na+]>CCO>[CH:25]1([O:24][C:18]2[C:19]([CH3:23])=[CH:20][CH:21]=[CH:22][C:17]=2[C:16]([NH:15][C:6]2([CH2:5][C:4]([OH:30])=[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]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 59314389HCID 59314389, compound

Product 1

HCID 25161050HCID 25161050, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the 2-(2-cyclobutyloxy-3-methylbenzoylamino)indan-2-acetic acid ethyl ester (288) (400 mg-1 mmol) in EtOH (15 mL)/water (1 mL) is treated with NaOH pellets (800 mg-20 mmol) and stirred at RT for 24 h. After concentration in vacuo, the residue is dissolved in water (30 mL) and acidified with HCl to pH 2-3. The product is extracted into EtOAc (3×20 mL) and the combined extracts washed with water (2×10 mL) and brine (2×15 mL). The organic layer is dried over MgSO4 and concentrated in vacuo. The residue is triturated with heptane and the pure product isolated by filtration to give white solid (350 mg, 92%).

Workup

  1. concentrationAfter concentration in vacuo
  2. dissolutionthe residue is dissolved in water (30 mL)
  3. extractionThe product is extracted into EtOAc (3×20 mL)
  4. washthe combined extracts washed with water (2×10 mL) and brine (2×15 mL)
  5. dry with materialThe organic layer is dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is triturated with heptane
  8. customthe pure product isolated by filtration

Sources & evidence

ORD record
ord-30a30794e03141a58cd97b027855684c
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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