Sodium Hydroxide → HCID 19348746, compound

HRID 1418222Notes

Reaction equation

HRID 1418222 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:35])[CH2:19][CH:20]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:27]=1[O:33][CH3:34])[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:35])[CH2:19][CH:20]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][C:27]=1[O:33][CH3:34])[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])([CH3:4])([CH3:5])[CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19348644HCID 19348644, compound

Product 1

HCID 19348746HCID 19348746, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.0 ml (6.0 mmol) of a 2N aqueous aqueous solution of sodium hydroxide were added to a solution of 1.11 g (2.34 mmol) of N-(2-t-butyl-5-methoxycarbonylphenyl)-3-(2-methoxy-4-methylphenyl)octanamide [prepared as described in step (ii) above] in 30 ml of methanol, and the resulting mixture was heated under reflux for 1 hour, after which the solvent was removed by distillation under reduced pressure. The resulting residue was acidified with 1N aqueous hydrochloric acid, and the aqueous mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, afterwhich it was dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, giving 1.02 g (a quantitative yield) of the title compound as crystals, melting at 163.5°-165° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customafter which the solvent was removed by distillation under reduced pressure
  4. extractionthe aqueous mixture was extracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride, afterwhich it
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-bf08ecf695c7473cbddea6a0fd3418ef
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

Loading…