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

HRID 1081236

Reaction equation

HRID 1081236 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>C(Cl)Cl.[Au]>[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-f2fdda7ab4c84b9aab88acc15e48ddac
Source dataset
uspto-grants-1996_12
Patent number
US05585328

Linked notes

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