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

HRID 623680Notes

Reaction equation

HRID 623680 reaction equation
[C:1]([O:5][C:6](=[O:51])[N:7]([C:21]1[N:22]([C:26]2[CH:31]=[C:30]([CH:32]([CH3:34])[CH3:33])[C:29]([O:35]CC3C=CC=CC=3)=[CH:28][C:27]=2[O:43]CC2C=CC=CC=2)[N:23]=[N:24][CH:25]=1)[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>CCO.[OH-].[OH-].[Pd+2]>[OH:43][C:27]1[CH:28]=[C:29]([OH:35])[C:30]([CH:32]([CH3:34])[CH3:33])=[CH:31][C:26]=1[N:22]1[C:21]([N:7]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:13][CH:14]=2)[C:6](=[O:51])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:25][N:24]=[N:23]1

Participants

4

Reactant 1

HCID 117677922[3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-(4-morpholin-4-yl-benzyl)-carbamic acid t-butyl ester

Product 1

HCID 117678674tert-butyl 1-(2,4-dihydroxy-5-isopropylphenyl)-1H-1,2,3-triazol-5-yl(4-morpholinobenzyl)carbamate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of Pd(OH)2/C (0.02 mmol), [3-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-3H-[1,2,3]triazol-4-yl]-(4-morpholin-4-yl-benzyl)-carbamic acid t-butyl ester (138 mg, 0.2 mmol) in EtOH (5 ml) was subjected to one atmosphere of H2 for 1 hour. The catalyst was filtered off through Celite® pad and ethanol was then 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 then removed under reduced pressure
  3. customThe crude reaction mixture
  4. customwas used in the next reaction without any purification

Sources & evidence

ORD record
ord-55e2cc94cd0046b4a86a2eb83d3dd6b6
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Reaction notes

Loading…