Trifluoroacetic acid → Methyl 3-(aminosulfonyl)-1-methyl-1H-pyrrole-2-carboxylate

HRID 815

Reaction equation

HRID 815 reaction equation
CC([NH:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[C:15]([O:17][CH3:18])=[O:16])(=[O:8])=[O:7])(C)C.FC(F)(F)C(O)=O>[Au].C(Cl)Cl>[NH2:5][S:6]([C:9]1[CH:13]=[CH:12][N:11]([CH3:14])[C:10]=1[C:15]([O:17][CH3:18])=[O:16])(=[O:8])=[O:7]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19693837Methyl 3-[[(1,1-dimethylethyl)amino]sulfonyl]-1-methyl-1H-pyrrole-2-carboxylate

Product 1

HCID 15790324Methyl 3-(aminosulfonyl)-1-methyl-1H-pyrrole-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23985GoldCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.53 g of methyl 3-[[(1,1-dimethylethyl)amino]-sulfonyl]-1-methyl-1H-pyrrole-2-carboxylate in 40 mL, of methylene chloride under an nitrogen atmosphere was added 80 mL of trifluoroacetic acid (TFA). The gold solution was stirred at room temperature overnight ca. 16 hours. The gold solution was concentrated to an oily residue. Diethyl ether was added to the residue and removed by evaporation to remove residual TFA. The resulting solid was suspended in diethyl ether and filtered affording the title compound as a tan solid, m.p. 105°-107° C.

Workup

  1. concentrationThe gold solution was concentrated to an oily residue
  2. additionDiethyl ether was added to the residue
  3. customremoved by evaporation
  4. customto remove residual TFA
  5. filtrationfiltered

Sources & evidence

ORD record
ord-740719404b1e4815a4a77e34574adcd7
Source dataset
uspto-grants-1998_03
Patent number
US05723410

Linked notes

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