Water → [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

HRID 623674Notes

Reaction equation

HRID 623674 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([N:23]=[N+:24]=[N-:25])=[CH:11][C:10]=1[CH:26]([CH3:28])[CH3:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([O:33][C:34](=[O:50])[N:35]([C:48]#[CH:49])[C:36]1[CH:41]=[CH:40][C:39]([N:42]2[CH2:47][CH2:46][O:45][CH2:44][CH2:43]2)=[CH:38][CH:37]=1)([CH3:32])([CH3:31])[CH3:30].CCOC(C)=O.O>CN(C=O)C>[C:29]([O:33][C:34](=[O:50])[N:35]([C:48]1[N:23]([C:12]2[CH:11]=[C:10]([CH:26]([CH3:28])[CH3:27])[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:14][C:13]=2[O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:24]=[N:25][CH:49]=1)[C:36]1[CH:37]=[CH:38][C:39]([N:42]2[CH2:43][CH2:44][O:45][CH2:46][CH2:47]2)=[CH:40][CH:41]=1)([CH3:32])([CH3:31])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 67985290Ethynyl-(4-morpholin-4-yl-phenyl)-carbamic acid t-butyl esterHCID 715342021,5-Bis-benzyloxy-2-isopropyl-4-azido-benzene

Product 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 esterYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1,5-bis-benzyloxy-2-isopropyl-4-azido-benzene (373 mg, 1 mmol) and ethynyl-(4-morpholin-4-yl-phenyl)-carbamic acid t-butyl ester (275 mg, 0.91 mmol) in DMF (2.5 ml) was flushed with nitrogen three times as previously described before adding [Cp*Ru]4 (49 mg, 0.045 mmol) and repeating the three cycle-degassing with nitrogen. The reaction mixture was stirred at RT until completion (i.e., monitored by TLC). AcOEt and H2O were then added. The organic phase was extracted four times with AcOEt, washed with water (three times) and brine (once) and dried over Na2SO4. The solvent was removed under reduced pressure and the reaction mixture was purified by column chromatography (PE/AcOEt:60/40). The title compound was obtained as an oil.

Workup

  1. extractionThe organic phase was extracted four times with AcOEt
  2. washwashed with water (three times) and brine (once) and
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed under reduced pressure
  5. customthe reaction mixture was purified by column chromatography (PE/AcOEt:60/40)

Sources & evidence

ORD record
ord-9b1d09c803e44762a33b85a15dc5b346
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Reaction notes

Loading…