Tert-butyl 2-(2-(benzyloxy)-5-(3-(4-methylpiperazin-1-yl)propoxy)benzamido)-4-phenylbenzoate → Tert-butyl 2-(2-hydroxy-5-(3-(4-methylpiperazin-1-yl)propoxy)benzamido)-4-phenylbenzoate

HRID 454654Notes

Reaction equation

HRID 454654 reaction equation
C([O:8][C:9]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]2)=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:12])C1C=CC=CC=1>CO.C(Cl)(Cl)Cl.[C].[Pd]>[OH:8][C:9]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH2:40][N:41]2[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH2:42]2)=[CH:33][C:10]=1[C:11]([NH:13][C:14]1[CH:26]=[C:25]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:24]=[CH:23][C:15]=1[C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])=[O:12]

Participants

5

Reactant 1

HCID 66990152Tert-butyl 2-(2-(benzyloxy)-5-(3-(4-methylpiperazin-1-yl)propoxy)benzamido)-4-phenylbenzoate

Product 1

HCID 58508445Tert-butyl 2-(2-hydroxy-5-(3-(4-methylpiperazin-1-yl)propoxy)benzamido)-4-phenylbenzoateYield 51.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalyst4×HCID 887MethanolSolvent2×HCID 6212ChloroformSolvent2×

Procedure

To a solution mixture of the obtained tert-butyl 2-(2-(benzyloxy)-5-(3-(4-methylpiperazin-1-yl)propoxy)benzamido)-4-phenylbenzoate (0.059 g) in methanol (1.0 mL) and chloroform (1.0 mL), 10% palladium-carbon (0.023 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 1 hour and 20 minutes. To the reaction mixture, 10% palladium-carbon (0.058 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 3 hours. Methanol (2.0 mL), chloroform (2.0 mL), and 10% palladium-carbon (0.055 g) were added to the reaction mixture, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours and 50 minutes. To the reaction mixture, 10% palladium-carbon (0.025 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 4 hours and 30 minutes. The insoluble substance was removed by filtration, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol] to obtain 0.026 g of tert-butyl 2-(2-hydroxy-5-(3-(4-methylpiperazin-1-yl)propoxy)benzamido)-4-phenylbenzoate.

Workup

  1. additionwas added
  2. stirringby stirring under a hydrogen atmosphere at room temperature for 3 hours
  3. stirringby stirring under a hydrogen atmosphere at room temperature for 2 hours and 50 minutes
  4. stirringby stirring under a hydrogen atmosphere at room temperature for 4 hours and 30 minutes
  5. customThe insoluble substance was removed by filtration
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol]

Sources & evidence

ORD record
ord-e97768ed7bd24789a72ef316a43b9bf0
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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