Dimethyl Sulfate → Acetic acid (4-cyano-3-fluoro-phenyl)-(3-methyl-3h-imidazol-4-yl)-methyl ester

HRID 1594889Notes

Reaction equation

HRID 1594889 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([O:34][C:35](=[O:37])[CH3:36])[C:10]2[N:11]=[CH:12][N:13](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:14]=2)=[CH:5][C:4]=1[F:38])#[N:2].S(OC)(O[CH3:43])(=O)=O>CCOC(C)=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([O:34][C:35](=[O:37])[CH3:36])[C:10]2[N:11]([CH3:43])[CH:12]=[N:13][CH:14]=2)=[CH:5][C:4]=1[F:38])#[N:2]

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 11016583Acetic acid (4-cyano-3-fluoro-phenyl)-(1-trityl-1h-imidazol-4-yl)-methyl ester

Product 1

HCID 53810060Acetic acid (4-cyano-3-fluoro-phenyl)-(3-methyl-3h-imidazol-4-yl)-methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

Acetic acid (4-cyano-3-fluoro-phenyl)-(1-trityl-1H-imidazol-4-yl)-methyl ester (as described in Step C above) (4.60 g, 9.17 mmol) and dimethyl sulfate (0.83 mL, 8.81 mmol) were dissolved in EtOAc (20 mL) and heated at 60° C. overnight under Ar. The reaction was concentrated in vacuo, diluted with MeOH (30 mL), and refluxed for 1 hr, concentrated in vacuo and purified using SiO2 chromatography (0.5-4% MeOH/CH2Cl2 with NH4OH) to give the title compound.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. additiondiluted with MeOH (30 mL)
  3. temperaturerefluxed for 1 hr
  4. concentrationconcentrated in vacuo
  5. custompurified

Sources & evidence

ORD record
ord-97e5fecdf42e4434bc244b9154064694
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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