Sodium borohydride → 2-[4-(1-Hydroxyethyl)benzoylamino]-N-(4-methoxyphenyl)benzamide

HRID 395712Notes

Reaction equation

HRID 395712 reaction equation
[C:1]([C:4]1[CH:29]=[CH:28][C:7]([C:8]([NH:10][C:11]2[CH:27]=[CH:26][CH:25]=[CH:24][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[O:14])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[OH:3][CH:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([NH:10][C:11]2[CH:27]=[CH:26][CH:25]=[CH:24][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)=[O:14])=[O:9])=[CH:28][CH:29]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 106439802-(4-Acetylbenzoylamino)-N-(4-methoxyphenyl)benzamide

Product 1

HCID 106204192-[4-(1-Hydroxyethyl)benzoylamino]-N-(4-methoxyphenyl)benzamideYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(4-acetylbenzoylamino)-N-(4-methoxyphenyl)benzamide (101 mg, 0.260 mmol) in methanol (5 mL) cooled to 0° C. was added sodium borohydride (17 mg, 0.46 mmol). After 20 min, the reaction mixture was quenched with saturated aqueous ammonium chloride solution (1 mL), diluted with methylene chloride (30 mL), and washed with water. The organic layer was dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was chromatographed (silica gel, 25% ethyl acetate/75% hexanes to 50% ethyl acetate/50% hexanes) to give 85 mg (84%) of the title compound as a yellow solid.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous ammonium chloride solution (1 mL)
  2. additiondiluted with methylene chloride (30 mL)
  3. washwashed with water
  4. dry with materialThe organic layer was dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed (silica gel, 25% ethyl acetate/75% hexanes to 50% ethyl acetate/50% hexanes)

Sources & evidence

ORD record
ord-d9d470144fb84d658fdd6d9ffcd8b272
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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