Trifluoroacetic acid → Methyl 3-aminofuran-2-carboxylate

HRID 390810Notes

Reaction equation

HRID 390810 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:6][CH:7]=[CH:8][C:9]=1[NH:10]C(=O)OC(C)(C)C)=[O:4].FC(F)(F)C(O)=O>ClCCl>[NH2:10][C:9]1[CH:8]=[CH:7][O:6][C:5]=1[C:3]([O:2][CH3:1])=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 52987670Methyl 3-((tert-butoxycarbonyl)amino)furan-2-carboxylate

Product 1

HCID 45790120Methyl 3-aminofuran-2-carboxylateYield 86.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 2-(methoxycarbonyl)furan-3-ylcarbamate 33 (1.14 g, 1.0 eq) was dissolved in dichloromethane (8 ml) and treated with trifluoroacetic acid (5 ml). Reaction mixture was stirred at room temperature for 3 h, and was then concentrated. Residue was dissolved in dichloromethane and washed with saturated aq. NaHCO3. The organic layer was dried (Na2SO4) and concentrated Mixture was extracted with ethyl acetate. The combined organic extracts were dried with Na2SO4 and concentrated. The crude reaction mixture was purified by flash chromatography to yield methyl 3-aminofuran-2-carboxylate 34 (574 mg, 86%): MS (Q1) 142 (M)+.

Workup

  1. customReaction mixture
  2. concentrationwas then concentrated
  3. dissolutionResidue was dissolved in dichloromethane
  4. washwashed with saturated aq. NaHCO3
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. concentrationconcentrated Mixture
  7. extractionwas extracted with ethyl acetate
  8. dry with materialThe combined organic extracts were dried with Na2SO4
  9. concentrationconcentrated
  10. customThe crude reaction mixture
  11. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-c57c55defa9c4334889be0fb5fb5d5d9
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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