Acetone → N-(2-t-Butyl-5-carbamoylphenyl)-3-[4-(1-hydroxybutyl)-2-methoxyphenyl]octanamide

HRID 1637458Notes

Reaction equation

HRID 1637458 reaction equation
[BH4-].[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]([C:31](=[O:35])[CH2:32][CH2:33][CH3:34])=[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].CC(C)=O.C(OCC)(=O)C>C(O)C.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]([CH:31]([OH:35])[CH2:32][CH2:33][CH3:34])=[CH:27][C:26]=1[O:36][CH3:37])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])([CH3:5])([CH3:6])[CH3:4]

Participants

7

Reactant 4

HCID 180AcetoneHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 19348622N-(2-t-Butyl-5-carbamoylphenyl)-3-[4-(1-oxobutyl)-2-methoxyphenyl]octanamide

Product 1

HCID 19348575N-(2-t-Butyl-5-carbamoylphenyl)-3-[4-(1-hydroxybutyl)-2-methoxyphenyl]octanamideYield 98%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

70 mg (1.85 mmol) of sodium borohydride were added to a solution of 207 mg (0.418 mmol) of N-(2-t-butyl-5-carbamoylphenyl)-3-[4-(1-oxobutyl)-2-methoxyphenyl]octanamide (prepared as described in Example 99) in 5 ml of ethanol, and the resulting mixture was stirred for 3.5 hours. At the end of this time, the mixture was ice-cooled, acetone was added to the reaction mixture to decompose any excess of the reagent, and the solvent was removed by distillation under reduced pressure. The resulting residue was mixed with water and then extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was then removed by evaporation under reduced pressure. The residue thus obtained was purified by column chromatography through 15 g of silica gel using a gradient elution method, with mixtures of ethyl acetate and methanol ranging from 20:0 to 20:1 by volume as the eluent, to give 203 mg (yield 98%) of the title compound as crystals, melting at 153-155° C.

Workup

  1. temperaturecooled
  2. customthe solvent was removed by distillation under reduced pressure
  3. additionThe resulting residue was mixed with water
  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. customThe solvent was then removed by evaporation under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by column chromatography through 15 g of silica gel using
  10. washa gradient elution method

Sources & evidence

ORD record
ord-67ca2b8d267641838a9c37d58459d630
Source dataset
uspto-grants-2000_03
Patent number
US06040339

Reaction notes

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