Trifluoroacetic anhydride → HCID 67223534, compound

HRID 2359985Notes

Reaction equation

HRID 2359985 reaction equation
[C:1]([O:5][C:6](=[O:29])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:16][CH:15]=[C:14]2[CH2:24][CH2:25][C:26](=O)[NH2:27])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCOCC1.N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:29])[C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[CH:16][CH:15]=[C:14]2[CH2:24][CH2:25][C:26]#[N:27])=[CH:9][CH:8]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 672032314-[2-(2-Carbamoyl-ethyl)-5-phenylpyrrol-1-yl]-benzoic acid tert-butyl ester

Product 1

HCID 67223534HCID 67223534, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of 4-[2-(2-carbamoyl-ethyl)-5-phenylpyrrol-1-yl]-benzoic acid tert-butyl ester (3.92 mmol, 1.0 eq.) in dioxane and pyridine was cooled in an ice bath. To the mixture was added Trifluoroacetic anhydride (TFA, 7.84 mmol, 2.0 eq.). After 10 minutes the ice bath was removed and the reaction was allowed to warm to room temperature overnight. The solvent was evaporated in vacuo and the residue treated with EtOAc (250 mL) and saturated NaHCO3 (150 mL). The organic layer was separated, dried (Na2SO4) and the solvent evaporated in vacuo. The residue was loaded onto a 40 g RediSep silica-gel column for purification. Gradient elution with ethyl acetate/hexane (0% to 10% ethyl acetate in hexane over 25 minutes) gave the product as a yellow solid after combination of the appropriate fractions and evaporation of the solvent in vacuo, 62% yield.

Workup

  1. customAfter 10 minutes the ice bath was removed
  2. customThe solvent was evaporated in vacuo
  3. additionthe residue treated with EtOAc (250 mL) and saturated NaHCO3 (150 mL)
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customthe solvent evaporated in vacuo
  7. customThe residue was loaded onto a 40 g RediSep silica-gel column for purification
  8. washGradient elution with ethyl acetate/hexane (0% to 10% ethyl acetate in hexane over 25 minutes)

Sources & evidence

ORD record
ord-e0b53c4dc61843a7825b32151770ffba
Source dataset
uspto-grants-2014_04
Patent number
US08686015B2

Reaction notes

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