Sodium Hydroxide → HCID 18791401, compound

HRID 1005597Notes

Reaction equation

HRID 1005597 reaction equation
C([O:4][C:5]1[CH:49]=[CH:48][CH:47]=[CH:46][C:6]=1[C:7]([NH:9][C:10]1[CH:43]=[CH:42][C:13]([C:14]([N:16]([CH3:41])[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=2[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([N:32]2[CH2:37][CH2:36][CH:35]([N:38]([CH3:40])[CH3:39])[CH2:34][CH2:33]2)=[O:31])=[O:15])=[CH:12][C:11]=1[O:44][CH3:45])=[O:8])(=O)C.[OH-].[Na+]>CO>[OH:4][C:5]1[CH:49]=[CH:48][CH:47]=[CH:46][C:6]=1[C:7]([NH:9][C:10]1[CH:43]=[CH:42][C:13]([C:14]([N:16]([CH3:41])[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=2[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([N:32]2[CH2:37][CH2:36][CH:35]([N:38]([CH3:40])[CH3:39])[CH2:34][CH2:33]2)=[O:31])=[O:15])=[CH:12][C:11]=1[O:44][CH3:45])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18791303HCID 18791303, compound

Product 1

HCID 18791401HCID 18791401, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 4-[2-(acetyloxy)benzoyl]amino-3-methoxy-N-methyl-N-[2-[5-(4-dimethylaminopiperidin-1-yl)carbonylpent-1-yloxy]-4-methylphenyl]benzamide (400 mg) in methanol (10 ml) was treated with 1N sodium hydroxide solution (3 ml) at ambient temperature. After 6 hours, the reaction mixture was concentrated in vacuo and extracted with the mixture of dichloromethane and diluted hydrochloric acid. The organic phase was washed with brine and dried over sodium sulfate. The crude product was purified by silica gel column chromatography (SiO2 30 g, 5% methanol in chloroform) to give 4-[2-(hydroxy)benzoyl]amino-3-methoxy-N-methyl-N-[2-[5-(4-dimethylaminopiperidin-1-yl)carbonylpent-1-yloxy]-4-methylphenyl]benzamide (290 mg).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. extractionextracted with the mixture of dichloromethane and diluted hydrochloric acid
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customThe crude product was purified by silica gel column chromatography (SiO2 30 g, 5% methanol in chloroform)

Sources & evidence

ORD record
ord-98c005f7f91048569c4ab7aced024e14
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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