Sodium Hydroxide → HCID 19348540, compound

HRID 1418231Notes

Reaction equation

HRID 1418231 reaction equation
[OH-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])=[CH:9][C:8]=1[NH:20][C:21](=[O:39])[CH2:22][CH:23]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[C:30]=1[O:37][CH3:38])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])([CH3:6])([CH3:5])[CH3:4]>C(O)C>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:9][C:8]=1[NH:20][C:21](=[O:39])[CH2:22][CH:23]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[C:30]=1[O:37][CH3:38])[CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])([CH3:4])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19348612HCID 19348612, compound

Product 1

HCID 19348540HCID 19348540, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5 ml of an aqueous solution containing 490 mg (12.2 mmol) of sodium hydroxide were added to a solution of 1.56 g (3.05 mmol) of N-[2-t-butyl-5-(2-ethoxycarbonylethyl)phenyl]-3-(2,3-dimethoxyphenyl)octanamide (prepared as described in Preparation 76) in 15 ml of ethanol, and the resulting mixture was stirred at room temperature for 13 hours. At the end of this time, the solvent was removed by distillation under reduced pressure, and the resulting residue was dissolved in water. The aqueous mixture was then washed with diethyl ether. The aqueous phase was acidified with hydrochloric acid and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give 1.45 g (yield 98%) of the title compound as a foam-like substance.

Workup

  1. customAt the end of this time, the solvent was removed by distillation under reduced pressure
  2. dissolutionthe resulting residue was dissolved in water
  3. washThe aqueous mixture was then washed with diethyl ether
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customafter which the solvent was removed by distillation under reduced pressure
  8. customThe residue was purified by column chromatography through silica gel
  9. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-55fe89d545ee4801a9bc5d65db810f2c
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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