Nitric Acid → Ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-2-(1-isopropoxycarbonyloxy-2-methylpropyl)-2H-1,2,3-triazole-4-carboxylate

HRID 841965Notes

Reaction equation

HRID 841965 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([CH:33]=[CH:34][C:35]=1[O:36][CH3:37])[C:10]([C:12]1[C:13]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:14][N:15]([CH:17]([O:21][C:22]([O:24][CH:25]([CH3:27])[CH3:26])=[O:23])[CH:18]([CH3:20])[CH3:19])[N:16]=1)=[O:11]>>[CH3:37][O:36][C:35]1[C:7]([O:6][CH3:5])=[CH:8][C:9]([C:10]([C:12]2[C:13]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[N:14][N:15]([CH:17]([O:21][C:22]([O:24][CH:25]([CH3:26])[CH3:27])=[O:23])[CH:18]([CH3:20])[CH3:19])[N:16]=2)=[O:11])=[C:33]([N+:1]([O-:4])=[O:2])[CH:34]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 22222597Ethyl 5-(3,4-dimethoxybenzoyl)-2-(1-isopropoxycarbonyloxy-2-methylpropyl)-2H-1,2,3-triazole-4-carboxylate

Product 1

HCID 22222564Ethyl 5-(4,5-dimethoxy-2-nitrobenzoyl)-2-(1-isopropoxycarbonyloxy-2-methylpropyl)-2H-1,2,3-triazole-4-carboxylate

Procedure

70% nitric acid (1 ml) was added to ethyl 5-(3,4-dimethoxybenzoyl)-2-(1-isopropoxycarbonyloxy-2-methylpropyl)-2H-1,2,3-triazole-4-carboxylate (86 mg, 0.19 mmol) as Intermediate 8 under ice cooling. The mixture was stirred at that temperature for 30 min. The reaction solution was poured into ice and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine solution in that order and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the title compound as a single compound (49 mg, 52%). The Rf value of thin-layer chromatography on silica gel and 1H-NMR spectrum were the same as those of the title compound of Example 20 (a).

Workup

  1. additionThe reaction solution was poured into ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine solution in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-87990a9e5b7e469dae2ccb292a7e7304
Source dataset
uspto-grants-2002_04
Patent number
US06372735B1

Reaction notes

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