[3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-5-ethylcarbamoyl-3H-[1,2,3]triazol-4-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester → [3-(2,4-dihydroxy-5-isopropyl-phenyl)-5-ethylcarbamoyl-3H-[1,2,3]triazol-4-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester

HRID 623685Notes

Reaction equation

HRID 623685 reaction equation
[C:1]([O:5][C:6](=[O:55])[N:7]([C:20]1[N:21]([C:30]2[CH:35]=[C:34]([CH:36]([CH3:38])[CH3:37])[C:33]([O:39]CC3C=CC=CC=3)=[CH:32][C:31]=2[O:47]CC2C=CC=CC=2)[N:22]=[N:23][C:24]=1[C:25](=[O:29])[NH:26][CH2:27][CH3:28])[C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>CCO.[OH-].[OH-].[Pd+2]>[C:1]([O:5][C:6](=[O:55])[N:7]([C:20]1[N:21]([C:30]2[CH:35]=[C:34]([CH:36]([CH3:37])[CH3:38])[C:33]([OH:39])=[CH:32][C:31]=2[OH:47])[N:22]=[N:23][C:24]=1[C:25](=[O:29])[NH:26][CH2:27][CH3:28])[C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[CH:12][CH:13]=1)([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 117678067[3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-5-ethylcarbamoyl-3H-[1,2,3]triazol-4-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 117678002[3-(2,4-dihydroxy-5-isopropyl-phenyl)-5-ethylcarbamoyl-3H-[1,2,3]triazol-4-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Intermediate obtained from Step C was hydrogenated for 1 hour in EtOH (5 ml) in the presence of Pd(OH)2/C (0.015 mmol). The catalyst was filtered off through Celite® pad and ethanol was removed under reduced pressure. The crude reaction mixture was used in the next reaction without any purification.

Workup

  1. filtrationThe catalyst was filtered off through Celite® pad and ethanol
  2. customwas removed under reduced pressure
  3. customThe crude reaction mixture
  4. customwas used in the next reaction without any purification

Sources & evidence

ORD record
ord-42d352c45d314ce8a88270881888faf9
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Reaction notes

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