Dichloromethane → HCID 19348451, compound

HRID 1418149Notes

Reaction equation

HRID 1418149 reaction equation
[OH-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[NH2:14])=[CH:9][C:8]=1[NH:16][C:17](=[O:38])[CH2:18][CH:19]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][O:32]C(=O)C)=[CH:27][C:26]=1[O:36][CH3:37])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])([CH3:6])([CH3:5])[CH3:4].C(Cl)Cl>CO>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:15])[NH2:14])=[CH:9][C:8]=1[NH:16][C:17](=[O:38])[CH2:18][CH:19]([C:25]1[CH:30]=[CH:29][C:28]([CH2:31][OH:32])=[CH:27][C:26]=1[O:36][CH3:37])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])([CH3:4])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 19348631HCID 19348631, compound

Product 1

HCID 19348451HCID 19348451, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

3.0 ml of a 2 N aqueous solution of sodium hydroxide were added to a solution of 2.25 g (4.95 mmol) of N-(2-t-Butyl-5-carbamoylphenyl)-3-(4-acetoxymethyl-2-methoxyphenyl)octanamide (prepared as described in Example 108) in 15 ml of methanol, and the resulting mixture was stirred for 40 minutes. At the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure, and the resulting residue was mixed with water. The aqueous mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of ammonium chloride and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through 100 g of silica gel using a gradient elution method, with mixtures of methylene chloride and methanol ranging from 12:1 to 10:1 by volume as the eluent, to give 1.99 g (yield 96%) of the title compound as a foam-like substance.

Workup

  1. distillationAt the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure
  2. additionthe resulting residue was mixed with water
  3. extractionThe aqueous mixture was extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of ammonium chloride and with a saturated aqueous solution of sodium chloride, in that order
  5. dry with materialafter which it was dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customthe resulting residue was purified by column chromatography through 100 g of silica gel using
  8. washa gradient elution method

Sources & evidence

ORD record
ord-6f3c1d516fc84ad2bd88e84db1fb1cd1
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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