HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → (3aR,6aS)-2-[5-amino-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrol-6-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | tert-butyl N-[5-[(3aR,6aS)-6-oxo-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrol-2-yl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate | HCID 66744152 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (3aR,6aS)-2-[5-amino-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrol-6-one | HCID 66744591 | — |
Reaction Steps
A solution of tert-butyl N-[5-[(3aR,6aS)-6-oxo-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrol-2-yl]-3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-N-tert-butoxycarbonyl-carbamate (57 mg, 0.10 mmol) in DCM (1 mL) was treated with TFA (1.5 g, 1 mL, 13 mmol) The reaction mixture was stirred at room temperature for 1 h. The solvents were evaporated and the residue was dissolved in DMF and purified by reverse phase column chromatography to obtain (3aR,6aS)-2-[5-amino-6-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrazin-2-yl]-1,3,3a,4,5,6a-hexahydrocyclopenta[c]pyrrol-6-one. LC/MS m/z 363.1 [M+H]+
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08410112B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-2c2421e4c3ab406eaf608716c50267ff |
| Source note | uspto-grants-2013_04 |