Isopropanol → Ethyl 5-(3,4-dimethoxybenzoyl)-2-(1-isopropoxycarbonyloxy-2-methylpropyl)-2H-1,2,3-triazole-4-carboxylate

HRID 1293559Notes

Reaction equation

HRID 1293559 reaction equation
O.[C:2]1([CH3:12])[CH:7]=CC(S(O)(=O)=O)=C[CH:3]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[C:18]([C:20]1[NH:24][N:23]=[N:22][C:21]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:19].C(N1C=CN=C1)(N1C=CN=C1)=O.FC(F)(F)[C:49]([OH:51])=[O:50].[CH:54]([OH:57])([CH3:56])[CH3:55]>C(Cl)Cl>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[C:18]([C:20]1[C:21]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N:22][N:23]([CH:7]([O:51][C:49]([O:57][CH:54]([CH3:56])[CH3:55])=[O:50])[CH:2]([CH3:3])[CH3:12])[N:24]=1)=[O:19]

Participants

7

Reactant 5

HCID 3776IsopropanolHCID 6422Trifluoroacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 521998p-Toluenesulfonic acid monohydrateHCID 178470512Ethyl 4-(3,4-dimethoxybenzoyl)-1H-1,2,3-triazole-5-carboxylate2×

Product 1

HCID 22222597Ethyl 5-(3,4-dimethoxybenzoyl)-2-(1-isopropoxycarbonyloxy-2-methylpropyl)-2H-1,2,3-triazole-4-carboxylateYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

p-Toluenesulfonic acid monohydrate (482 mg, 2.5 mmol) and isobutylaldehyde (3.4 ml, 37 mmol) were added to a solution of ethyl 5-(3,4-dimethoxybenzoyl)-1H-1,2,3-triazole-4-carboxylate (7.7 g, 25 mmol), prepared in the same manner as described above in connection with Intermediate 5, in methylene chloride (115 ml) under an argon atmosphere at −20° C. The mixture was stirred at −20° C. for one hr. Carbonyldiimidazole (6.2 g, 38 mmol) was added thereto, followed by stirred at −20° C. for additional one hr. Isopropyl alcohol (20 ml) was added thereto. The mixture was cooled to −30° C. Trifluoroacetic acid (5.8 ml, 75 mmol) was added thereto. The mixture was stirred at room temperature for 18 hr. The reaction solution was treated by a conventional method and purified by column chromatography on silica gel (hexane/ethyl acetate) to give the title compound as a colorless liquid (10.9 g, 93.4%).

Workup

  1. customprepared in the same manner
  2. stirringby stirred at −20° C. for additional one hr
  3. temperatureThe mixture was cooled to −30° C
  4. stirringThe mixture was stirred at room temperature for 18 hr
  5. additionThe reaction solution was treated by a conventional method
  6. custompurified by column chromatography on silica gel (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-435e9ee2d69f48d0a3292246768b51b2
Source dataset
uspto-grants-2007_07
Patent number
US07238812B2

Reaction notes

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