Trifluoroacetic acid → HCID 178468489, compound

HRID 1865102Notes

Reaction equation

HRID 1865102 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:35])[C:8]([CH2:33][CH3:34])=[C:9]([C:31]#[N:32])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([C:17]2[N:21](CC3C=CC(OC)=CC=3)[N:20]=[N:19][N:18]=2)=[CH:13][CH:12]=1)=[O:5])[CH3:2].C(O)(C(F)(F)F)=O>>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:35])[C:8]([CH2:33][CH3:34])=[C:9]([C:31]#[N:32])[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([C:17]2[NH:18][N:19]=[N:20][N:21]=2)=[CH:15][CH:16]=1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69020309HCID 69020309, compound

Product 1

HCID 178468489HCID 178468489, compoundYield 90.8%

Procedure

Into a round bottom flask containing 4-cyano-5-ethyl-3-{4-[1-(4-methoxybenzyl)-1H-tetrazol-5-yl]-phenyl}-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (0.15 g, 0.33 mmol, prepared in example E-241) add TFA (2 mL) and stir over night. Concentrate the mixture and azeotrope the residue with a mixture of methylene chloride/hexanes. Dilute the mixture with 0.500 N HCl (20 mL) and extract with ethyl acetate (3×30 mL). Combine the organic extracts, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue by silica gel chromatography (eluent: 0 to 5% MeOH/ethyl acetate). Concentrate the purified fractions under reduced pressure and place under vacuum to provide the title compound as a tan solid (0.105 g); mass spectrum (m/e): 351.05 (M+H)

Workup

  1. concentrationConcentrate the mixture
  2. additionwith a mixture of methylene chloride/hexanes
  3. additionDilute the mixture with 0.500 N HCl (20 mL)
  4. extractionextract with ethyl acetate (3×30 mL)
  5. dry with materialCombine the organic extracts, dry over anhydrous sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customPurify the residue by silica gel chromatography (eluent: 0 to 5% MeOH/ethyl acetate)
  9. concentrationConcentrate the purified fractions under reduced pressure and place under vacuum

Sources & evidence

ORD record
ord-2a78aab413844997a4b56a8f033621df
Source dataset
uspto-grants-2009_12
Patent number
US07625932B2

Reaction notes

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