Water → 1-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-5-[tert-butoxycarbonyl-(4-morpholin-4-yl-phenyl)-amino]-1H-[1,2,3]triazole-4-carboxylic acid methyl ester

HRID 623683Notes

Reaction equation

HRID 623683 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.[CH3:29][O:30][C:31](=[O:54])[C:32]#[C:33][N:34]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:35]1[CH:40]=[CH:39][C:38]([N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)=[CH:37][CH:36]=1.CCOC(C)=O.O>CN(C=O)C>[CH3:29][O:30][C:31]([C:32]1[N:25]=[N:24][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)[C:33]=1[N:34]([C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48])[C:35]1[CH:36]=[CH:37][C:38]([N:41]2[CH2:42][CH2:43][O:44][CH2:45][CH2:46]2)=[CH:39][CH:40]=1)=[O:54]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 715342021,5-Bis-benzyloxy-2-isopropyl-4-azido-benzeneHCID 117677873[Tert-butoxycarbonyl-(4-morpholin-4-yl-phenyl)-amino]-propynoic acid methyl ester

Product 1

HCID 1176778751-(2,4-bis-benzyloxy-5-isopropyl-phenyl)-5-[tert-butoxycarbonyl-(4-morpholin-4-yl-phenyl)-amino]-1H-[1,2,3]triazole-4-carboxylic acid methyl esterYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1,5-bis-benzyloxy-2-isopropyl-4-azido-benzene (373 mg, 1 mmol) and [t-butoxycarbonyl-(4-morpholin-4-yl-phenyl)-amino]-propynoic acid methyl ester (328 mg, 0.91 mmol) in DMF (2.5 ml) was degassed at RT by means of three vacuum-nitrogen cycles before adding [Cp*RuCl]4 (49 mg, 0.045 mmol) and repeating the three degassing cycles 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-0cc8ce49dcbe41b6abc2f1a5eea25699
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Reaction notes

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