Trifluoroacetic anhydride → 4H,5H,6H-7lambda5-pyrrolo[1,2-c][1,2,3]oxadiazol-7-ylium-3-olate

HRID 2307250Notes

Reaction equation

HRID 2307250 reaction equation
[N+:1]([N:4]1[CH2:11][CH2:10][CH2:9][C@H:5]1[C:6]([OH:8])=[O:7])([O-])=O.FC(F)(F)C(OC(=O)C(F)(F)F)=O>CCOCC>[N:1]1[O:7][C:6]([O-:8])=[C:5]2[CH2:9][CH2:10][CH2:11][N+:4]=12

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 211172671-Nitro-L-proline

Product 1

HCID 150890374H,5H,6H-7lambda5-pyrrolo[1,2-c][1,2,3]oxadiazol-7-ylium-3-olate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N-Nitroproline (17.0 g, 118 mmol) was suspended in ether (400 ml) and cooled in ice. Trifluoroacetic anhydride (16.5 ml, 120 mmol) was then added dropwise over 30 minutes and the mixture left to warm to room temperature whilst stirring over 16 hours. The mixture was evaporated in vacuo to an oil and purified by column chromatography on silica gel using an eluant of ethyl acetate to afford the title compound, 9.8 g.

Workup

  1. temperaturecooled in ice
  2. waitthe mixture left
  3. customThe mixture was evaporated in vacuo to an oil
  4. custompurified by column chromatography on silica gel using an eluant of ethyl acetate

Sources & evidence

ORD record
ord-dd8f782405ce47f28831dfbf6f7f42ff
Source dataset
uspto-grants-2004_12
Patent number
US06831074B2

Reaction notes

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