Tert-butyl 2-(2-(benzyloxy)-5-((1-methylpiperidin-4-yl)oxy)benzamido)-4-phenylbenzoate → HCID 58508711, compound

HRID 454622Notes

Reaction equation

HRID 454622 reaction equation
C([O:8][C:9]1[CH:36]=[CH:35][C:34]([O:37][CH:38]2[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]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>[C].[Pd].CO>[OH:8][C:9]1[CH:36]=[CH:35][C:34]([O:37][CH:38]2[CH2:39][CH2:40][N:41]([CH3:44])[CH2:42][CH2:43]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]

Participants

4

Reactant 1

HCID 66991124Tert-butyl 2-(2-(benzyloxy)-5-((1-methylpiperidin-4-yl)oxy)benzamido)-4-phenylbenzoate

Product 1

HCID 58508711HCID 58508711, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a methanol (5.0 mL) solution of the obtained tert-butyl 2-(2-(benzyloxy)-5-((1-methylpiperidin-4-yl)oxy)benzamido)-4-phenylbenzoate, 10% palladium-carbon (0.11 g) was added, followed by stirring under a hydrogen atmosphere at room temperature for 2 hours and 40 minutes. The insoluble substance was removed by filtration, and the obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol] to obtain 0.13 g of tert-butyl 2-(2-hydroxy-5-((1-methylpiperidin-4-yl)oxy)benzamido)-4-phenylbenzoate as a light yellow solid.

Workup

  1. customThe insoluble substance was removed by filtration
  2. customthe obtained residue was purified by silica gel column chromatography [eluent: 100-90% chloroform/methanol]

Sources & evidence

ORD record
ord-b3d056cc19564e08a2f14d2f6bc84788
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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