Methyl 2-(2-(benzyloxy)-5-(2-(diethylamino)ethoxy)benzamido)-4-phenylbenzoate → Methyl 2-(5-(2-(diethylamino)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoate

HRID 454664Notes

Reaction equation

HRID 454664 reaction equation
C([O:8][C:9]1[CH:33]=[CH:32][C:31]([O:34][CH2:35][CH2:36][N:37]([CH2:40][CH3:41])[CH2:38][CH3:39])=[CH:30][C:10]=1[C:11]([NH:13][C:14]1[CH:23]=[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])=[O:12])C1C=CC=CC=1>CO.C(OCC)(=O)C.[C].[Pd]>[CH2:40]([N:37]([CH2:38][CH3:39])[CH2:36][CH2:35][O:34][C:31]1[CH:32]=[CH:33][C:9]([OH:8])=[C:10]([CH:30]=1)[C:11]([NH:13][C:14]1[CH:23]=[C:22]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])=[O:12])[CH3:41]

Participants

5

Reactant 1

HCID 66990476Methyl 2-(2-(benzyloxy)-5-(2-(diethylamino)ethoxy)benzamido)-4-phenylbenzoate

Product 1

HCID 58508834Methyl 2-(5-(2-(diethylamino)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoateYield 69.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution mixture of the obtained methyl 2-(2-(benzyloxy)-5-(2-(diethylamino)ethoxy)benzamido)-4-phenylbenzoate (0.15 g) in methanol (3.0 mL) and ethyl acetate (3.0 mL), 10% palladium-carbon (0.030 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 3 hours. 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: 100-96% chloroform/methanol] to obtain 0.087 g of methyl 2-(5-(2-(diethylamino)ethoxy)-2-hydroxybenzamido)-4-phenylbenzoate as a white solid.

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 [eluent: 100-96% chloroform/methanol]

Sources & evidence

ORD record
ord-d85e1386ec594ac29b2ea32b336a4784
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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