Tert-butyl 2-(2-(benzyloxy)-5-(methyl(2-(morpholin-4-yl)ethyl)amino)benzamido)-4-phenylbenzoate → Tert-butyl 2-(2-hydroxy-5-(methyl(2-(morpholin-4-yl)ethyl)amino)benzamido)-4-phenylbenzoate

HRID 454611Notes

Reaction equation

HRID 454611 reaction equation
C([O:8][C:9]1[CH:36]=[CH:35][C:34]([N:37]([CH3:46])[CH2:38][CH2:39][N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]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(OCC)(=O)C.[C].[Pd]>[OH:8][C:9]1[CH:36]=[CH:35][C:34]([N:37]([CH3:46])[CH2:38][CH2:39][N:40]2[CH2:41][CH2:42][O:43][CH2:44][CH2:45]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 66990678Tert-butyl 2-(2-(benzyloxy)-5-(methyl(2-(morpholin-4-yl)ethyl)amino)benzamido)-4-phenylbenzoate

Product 1

HCID 58508749Tert-butyl 2-(2-hydroxy-5-(methyl(2-(morpholin-4-yl)ethyl)amino)benzamido)-4-phenylbenzoateYield 72.1%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution mixture of the obtained tert-butyl 2-(2-(benzyloxy)-5-(methyl(2-(morpholin-4-yl)ethyl)amino)benzamido)-4-phenylbenzoate (0.12 g) in methanol (1.5 mL) and ethyl acetate (1.5 mL), 10% palladium-carbon (0.12 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours and 30 minutes. Ethyl acetate was added to the reaction mixture. The insoluble substance was removed by filtration, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-95% chloroform/methanol] to obtain 0.074 g of tert-butyl 2-(2-hydroxy-5-(methyl(2-(morpholin-4-yl)ethyl)amino)benzamido)-4-phenylbenzoate.

Workup

  1. additionwas added
  2. customThe insoluble substance was removed by filtration
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 100-95% chloroform/methanol]

Sources & evidence

ORD record
ord-c16b167330b84efa83ff15bcdd5d22e0
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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