Trifluoroacetic acid → HCID 70098375, compound

HRID 467624Notes

Reaction equation

HRID 467624 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:10]([N:11](C(OC(C)(C)C)=O)C(OC(C)(C)C)=O)=[N:9][CH:8]=[C:7]([CH2:26][CH:27]([CH3:29])[CH3:28])[N:6]=1)=[O:4].FC(F)(F)C(O)=O.CCCCCCC.C(OCC)(=O)C>ClCCl>[CH3:1][O:2][C:3]([C:5]1[C:10]([NH2:11])=[N:9][CH:8]=[C:7]([CH2:26][CH:27]([CH3:29])[CH3:28])[N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21899848Ethylacetate heptaneHCID 70096779HCID 70096779, compound

Product 1

HCID 70098375HCID 70098375, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(bis(tert-butoxycarbonyl)amino)-6-isobutylpyrazine-2-carboxylic acid methyl ester (201 mg, 442 μmol) in dichloromethane (4 mL) was added trifluoroacetic acid (511 μL, 6.63 mmol) at room temperature. The mixture was stirred at ambient temperature for 3 h and the volatiles were evaporated. The residue was dissolved in dichloromethane (50 mL) and extracted with sodium carbonate. The aqueous phase was washed with dichloromethane and the organic layers were dried and evaporated. The product was obtained after silica gel chromatography using a heptane/ethyl acetate gradient as light yellow solid (88 mg, 95%).

Workup

  1. customthe volatiles were evaporated
  2. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  3. extractionextracted with sodium carbonate
  4. washThe aqueous phase was washed with dichloromethane
  5. customthe organic layers were dried
  6. customevaporated
  7. customThe product was obtained after silica gel chromatography

Sources & evidence

ORD record
ord-9af187d9cd214afe9835599ff09a2369
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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