3-benzyloxy-N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-4-methyl-benzamide → N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-hydroxy-4-methyl-benzamide

HRID 1844589Notes

Reaction equation

HRID 1844589 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:32]=[CH:33][C:34]=1[CH3:35])[C:12]([NH:14][C:15]1[CH:20]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:18]=[C:17]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[C:16]=1[O:30][CH3:31])=[O:13])C1C=CC=CC=1.[H][H]>CO.O1CCCC1.[Pd]>[C:21]([C:19]1[CH:18]=[C:17]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[C:16]([O:30][CH3:31])=[C:15]([NH:14][C:12](=[O:13])[C:11]2[CH:32]=[CH:33][C:34]([CH3:35])=[C:9]([OH:8])[CH:10]=2)[CH:20]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

6

Reactant 2

HCID 672175483-benzyloxy-N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-4-methyl-benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 67217566N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-3-hydroxy-4-methyl-benzamide

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

7.10 g 3-benzyloxy-N-(5-tert-butyl-3-methanesulphonylamino-2-methoxy-phenyl)-4-methyl-benzamide are hydrogenated in a mixture of 70 ml of methanol and 40 ml of tetrahydrofuran in the presence of 800 mg palladium on activated charcoal (10% Pd) at ambient temperature and 50 psi partial hydrogen pressure. Then the catalyst is suction filtered and the filtrate is evaporated down using the rotary evaporator. A white solid remains, which is reacted further without any further purification.

Workup

  1. filtrationfiltered
  2. customthe filtrate is evaporated down
  3. customthe rotary evaporator
  4. customA white solid remains, which is reacted further without any further purification

Sources & evidence

ORD record
ord-8a8bbf35f9cb4885bf39e7313f6bfa02
Source dataset
uspto-grants-2015_02
Patent number
US08946438B2

Reaction notes

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