Imidazole → HCID 131726836, compound

HRID 901957Notes

Reaction equation

HRID 901957 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].OCC[NH:12][C:13]([CH:15]1[O:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[NH:17][CH2:16]1)=[O:14].N1[CH:29]=[CH:28]N=C1.CN(C=[O:34])C>C(OCC)(=O)C>[Si:1]([O:34][CH2:28][CH2:29][C:15]1([C:13]([NH2:12])=[O:14])[O:20][C:19]2[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=2[NH:17][CH2:16]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 43242556HCID 43242556, compound

Product 1

HCID 131726836HCID 131726836, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyldimethylsilyl chloride (135 mg, 0.9 mmol) was added to a solution of N-(2-hydroxyethyl)benzomorpholine-2-carboxamide (185 mg, 0.83 mmol) and imidazole (61 mg, 0.90 mmol) in DMF (3 ml) while cooling in an ice/water bath. The mixture was allowed to warm to room temperature and stirred for 18 h. The mixture was reduced, taken up in ethyl acetate, washed with 0.3N potassium hydrogen sulphate and brine, filtered through phase separation paper and reduced. Chromatography (70% EtOAc/30% 60-80 petroleum ether) afforded N-(2-(tert-butyldimethylsilyloxyethyl)benzomorpholine-2-carboxamide (230 mg, 82%) as a brown gum.

Workup

  1. temperaturewhile cooling in an ice/water bath
  2. washwashed with 0.3N potassium hydrogen sulphate and brine
  3. filtrationfiltered through phase separation paper

Sources & evidence

ORD record
ord-ddde13fd9ef84ae192daf57e23420317
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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