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Acetone → ethyl 2-(1-isopropoxycarbonyloxy-2-methylpropyl)-5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate

HRID 1794701
Notes
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Reaction equation

HRID 1794701 reaction equation
[I-].[Na+].[C:3](=[O:6])([O-])[O-].[K+].[K+].Cl[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11].[CH:16]([O:19][C:20]1[C:21]([O:41][CH3:42])=[CH:22][C:23]([N+:38]([O-:40])=[O:39])=[C:24]([CH:37]=1)[C:25]([C:27]1[NH:31][N:30]=[N:29][C:28]=1[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:26])([CH3:18])[CH3:17].[CH3:43][C:44]([CH3:46])=O>O>[CH:13]([O:12][C:10]([O:6][CH:3]([N:30]1[N:29]=[C:28]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:27]([C:25](=[O:26])[C:24]2[CH:37]=[C:20]([O:19][CH:16]([CH3:18])[CH3:17])[C:21]([O:41][CH3:42])=[CH:22][C:23]=2[N+:38]([O-:40])=[O:39])=[N:31]1)[CH:44]([CH3:46])[CH3:43])=[O:11])([CH3:15])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 180AcetoneHCID 5238Sodium IodideHCID 7917Isopropyl chloroformateHCID 11430Potassium CarbonateHCID 178470513HCID 178470513, compound

Product 1

HCID 22222605ethyl 2-(1-isopropoxycarbonyloxy-2-methylpropyl)-5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate
Yield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Isobutyl aldehyde (2.9 ml), sodium iodide (3.18 g), potassium carbonate (11.69 g), and isopropyl chloroformate (7.2 ml) were added in that order under an argon atmosphere at room temperature to a solution of ethyl 5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-4-carboxylate (8.01 g), prepared in step (32a), in acetone (150 ml). The mixture was stirred at that temperature for 19.5 hr. Water was added to the reaction mixture to stop the reaction. The mixture was extracted with ethyl acetate. The organic layer was washed with 20% saline and dried over anhydrous magnesium sulfate. The solvent was evaporated. The resultant mixture was purified by column chromatography on silica gel (hexane/ethyl acetate) to give ethyl 2-(1-isopropoxycarbonyloxy-2-methylpropyl)-5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate (10.12 g, 89%).

Workup

  1. customthe reaction
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with 20% saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customThe resultant mixture was purified by column chromatography on silica gel (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3267b2e8cb374f3fa9aa7e9afa845619
Source dataset
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07022860B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes