HCID 54493274, compound → HCID 19956158, compound

HRID 1779432Notes

Reaction equation

HRID 1779432 reaction equation
[C:1]1([S:7]([C:10]2[S:14][C:13]([NH:15]C(=O)OC(C)(C)C)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>FC(F)(F)C(O)=O>[NH2:15][C:13]1[S:14][C:10]([S:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:9])=[O:8])=[CH:11][CH:12]=1

Participants

3

Reactant 1

HCID 54493274HCID 54493274, compound

Product 1

HCID 19956158HCID 19956158, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl [5-(phenylsulfonyl)thien-2-yl]carbamate (0.37 g, 1.1 mmol) is dissolved in 5 ml of trifluoroacetic acid and the solution is stirred at room temperature for 2 hours. The trifluoroacetic acid is distilled off and the residue is partitioned between semisaturated sodium hydrogen carbonate solution and dichloromethane. The phases are separated and the aqueous phase is subjected to extraction with dichloromethane. The combined organic phases are dried over potassium carbonate and filtered and the solvent is distilled off.

Workup

  1. distillationThe trifluoroacetic acid is distilled off
  2. customthe residue is partitioned between semisaturated sodium hydrogen carbonate solution and dichloromethane
  3. customThe phases are separated
  4. extractionthe aqueous phase is subjected to extraction with dichloromethane
  5. dry with materialThe combined organic phases are dried over potassium carbonate
  6. filtrationfiltered
  7. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-e3edff32539e4596b6565eb6ab80958c
Source dataset
uspto-grants-1997_05
Patent number
US05627198

Reaction notes

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