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

HRID 623675Notes

Reaction equation

HRID 623675 reaction equation
[C:1]([O:5][C:6](=[O:50])[N:7]([C:20]1[N:21]([C:25]2[CH:30]=[C:29]([CH:31]([CH3:33])[CH3:32])[C:28]([O:34]CC3C=CC=CC=3)=[CH:27][C:26]=2[O:42]CC2C=CC=CC=2)[N:22]=[N:23][CH:24]=1)[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:50])[N:7]([C:20]1[N:21]([C:25]2[CH:30]=[C:29]([CH:31]([CH3:32])[CH3:33])[C:28]([OH:34])=[CH:27][C:26]=2[OH:42])[N:22]=[N:23][CH:24]=1)[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)([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 117678191[3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid t-butyl ester

Product 1

HCID 131735186[3-(2,4-dihydroxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid t-butyl ester

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Pd(OH)2/C (0.02 mmol) was added to [3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-(4-morpholin-4-yl-phenyl)-carbamic acid t-butyl ester (135 mg, 0.2 mmol) dissolved in EtOH (5 ml) and the mixture was subjected to one atmosphere of H2 for 1 hour. 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-70190a3af3524674b44aaf43e628926f
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Reaction notes

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