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

HRID 1959452Notes

Reaction equation

HRID 1959452 reaction equation
[O:1]=[C:2]1[C@@H:6]2[CH2:7][N:8]([C:10]3[N:11]=[C:12]([C:31]4[O:32][C:33]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)=[N:34][N:35]=4)[C:13]([N:16](C(OC(C)(C)C)=O)C(=O)OC(C)(C)C)=[N:14][CH:15]=3)[CH2:9][C@@H:5]2[CH2:4][CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:16][C:13]1[N:14]=[CH:15][C:10]([N:8]2[CH2:9][C@@H:5]3[CH2:4][CH2:3][C:2](=[O:1])[C@@H:6]3[CH2:7]2)=[N:11][C:12]=1[C:31]1[O:32][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[N:34][N:35]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66744152tert-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

Product 1

HCID 66744591(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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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]+

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue was dissolved in DMF
  3. custompurified by reverse phase column chromatography

Sources & evidence

ORD record
ord-2c2421e4c3ab406eaf608716c50267ff
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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