Sodium Hydroxide → HCID 19348635, compound

HRID 1637489Notes

Reaction equation

HRID 1637489 reaction equation
[OH-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([O:15]C)=[O:14])=[CH:9][C:8]=1[NH:17][C:18](=[O:36])[CH2:19][CH:20]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=1[O:34][CH3:35])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])([CH3:6])([CH3:5])[CH3:4]>CO>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][C:8]=1[NH:17][C:18](=[O:36])[CH2:19][CH:20]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=1[O:34][CH3:35])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])([CH3:4])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19348422N-(2-t-butyl-5-methoxycarbonylphenyl)-3-(2,4-dimethoxyphenyl)octanamide

Product 1

HCID 19348635HCID 19348635, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.5 ml (7.0 mmol) of a 2 N aqueous solution of sodium hydroxide were added to a solution of 1.64 g (3.48 mmol) of N-(2-t-butyl-5-methoxycarbonylphenyl)-3-(2,4-dimethoxyphenyl)octanamide (prepared as described in Preparation 6) in 30 ml of methanol, and the resulting mixture was heated under reflux for 2 hours, after which the solvent was removed by distillation under reduced pressure. The residue was acidified with 2 N aqueous hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was recrystallized from a mixture of ethyl acetate and hexane to give 1.13 g (yield 71%) of the title compound, melting at 153-154° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customafter which the solvent was removed by distillation under reduced pressure
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialafter which it was dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customthe resulting residue was recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-38789789ba3d47c0a8ba7008dc9c41f3
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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