Diazomethane → HCID 178418785, compound

HRID 1492496Notes

Reaction equation

HRID 1492496 reaction equation
C([C:5]1[N:6](O)[C:7]([C:14]([O:16][CH2:17]C)=[O:15])=[C:8](C(F)(F)F)[N:9]=1)CCC.[N+](=C)=[N-].S([O-])([O-])(=O)=O.[Mg+2]>CO.C(OCC)C>[NH:9]1[CH:8]=[C:7]([C:14]([O:16][CH3:17])=[O:15])[N:6]=[CH:5]1

Participants

6

Reactant 3

HCID 9550DiazomethaneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 9838586HCID 9838586, compound

Product 1

HCID 178418785HCID 178418785, compoundYield 136.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2-butyl-1-hydroxy-4-(trifluoromethyl)-1H-imidazole-5-carboxylic acid, ethyl ester (506 mg, 3.14 mmol) dissolved in a mixture of 5 mL of methanol and 10 mL of diethyl ether was added ethereal diazomethane until disappearance of starting acid was indicated by TLC. Anhydrous magnesium sulfate was then added and the solution filtered and concentrated in vacuo. Flash chromatography on 10 g of Merck silica gel eluted with 2:1, CHCl3 :hexanes, followed by 10:1, CHCl3 :Et2O afforded the title D compound (540 mg).

Workup

  1. filtrationthe solution filtered
  2. concentrationconcentrated in vacuo
  3. washFlash chromatography on 10 g of Merck silica gel eluted with 2:1, CHCl3

Sources & evidence

ORD record
ord-dcfcb80b162f4fffbac26287d0d5a2cb
Source dataset
uspto-grants-1994_12
Patent number
US05374615

Reaction notes

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