HCID 53732321, compound → HCID 15814262, compound

HRID 1779428Notes

Reaction equation

HRID 1779428 reaction equation
[C:1]1([C:7]([C:9]2[S:13][C:12]([NH:14]C(=O)OC(C)(C)C)=[CH:11][CH:10]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(=O)C>[NH2:14][C:12]1[S:13][C:9]([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[O:8])=[CH:10][CH:11]=1

Participants

3

Reactant 1

HCID 53732321HCID 53732321, compound

Product 1

HCID 15814262HCID 15814262, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

tert-Butyl [5-(phenylcarbonyl) thien-2-yl]carbamate (0.30 g, 0.99 mmol) is dissolved in 5 ml of trifluoroacetic acetic 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-f6d662c9ba89494380fe51923b5109fb
Source dataset
uspto-grants-1997_05
Patent number
US05627198

Reaction notes

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