Water → [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

HRID 623679Notes

Reaction equation

HRID 623679 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]([N:31]([CH2:39][C:40]1[CH:45]=[CH:44][C:43]([N:46]2[CH2:51][CH2:50][O:49][CH2:48][CH2:47]2)=[CH:42][CH:41]=1)[C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])#[CH:30].CCOC(C)=O.O>CN(C=O)C>[C:34]([O:33][C:32](=[O:38])[N:31]([C:29]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:30]=1)[CH2:39][C:40]1[CH:45]=[CH:44][C:43]([N:46]2[CH2:47][CH2:48][O:49][CH2:50][CH2:51]2)=[CH:42][CH:41]=1)([CH3:37])([CH3:36])[CH3:35]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 715342021,5-Bis-benzyloxy-2-isopropyl-4-azido-benzeneHCID 117677987t-Butyl ethynyl(4-morpholinobenzyl)carbamate

Product 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 esterYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1,5-bis-benzyloxy-2-isopropyl-4-azido-benzene (240 mg, 0.64 mmol) and t-butyl ethynyl(4-morpholinobenzyl)carbamate (185 mg, 0.58 mmol) in DMF (2.5 ml) was degassed at RT by means of three vacuum-nitrogen cycles before adding [Cp*RuCl]4 (32 mg, 0.029 mmol). 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-ccfaa19a3e524f72bfc203cfd5ab7acb
Source dataset
uspto-grants-2016_04
Patent number
US09302998B2

Reaction notes

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