Trifluoroacetic acid → HCID 53913605, compound

HRID 1701042Notes

Reaction equation

HRID 1701042 reaction equation
C(O[C:6](=O)[N:7]([C@@H:9]([C:17]1[O:18][C:19]([C:22](=[O:24])[NH2:23])=[N:20][N:21]=1)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:6][NH:7][C@@H:9]([C:17]1[O:18][C:19]([C:22]([NH2:23])=[O:24])=[N:20][N:21]=1)[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53673637HCID 53673637, compound

Product 1

HCID 53913605HCID 53913605, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

((1R)-1-(5-Carbamoyl-[1,3,4]oxadiazol-2-yl)-2-phenylethyl)methylcarbamic acid tert-butylester (350 mg, 1.01 mmol) was dissolved in dichloromethane (6 ml). The solution was cooled to 0° C. Trifluoroacetic acid (2 ml) was added dropwise. The solution was stirred for 30 min. The solvent was removed in vacuo. The residue was dissolved in dichloromethane (6 ml) and the solvent was removed in vacuo. The residue was again dissolved in dichloromethane (6 ml) and the solvent was removed in vacuo. The residue was dissolved in dichloromethane (10 ml). This phase was washed with water. The aqueous phase was lyophilized to give 247 mg of crude 5-((1R)-1-methylamino-2-phenylethyl)-[1,3,4]oxadiazole-2-carboxylic acid amide, which was used for the further synthesis.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (6 ml)
  3. customthe solvent was removed in vacuo
  4. dissolutionThe residue was again dissolved in dichloromethane (6 ml)
  5. customthe solvent was removed in vacuo
  6. dissolutionThe residue was dissolved in dichloromethane (10 ml)
  7. washThis phase was washed with water

Sources & evidence

ORD record
ord-70bbf5a8a99e49d58f4dc94c1b9129b7
Source dataset
uspto-grants-2002_02
Patent number
US06350767B1

Reaction notes

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