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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
Tricarballylic acid is an inhibitor of aconitase and therefore interferes with the Krebs cycle.
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CAS No. : | 99-14-9 |
Formula : | C6H8O6 |
M.W : | 176.12 |
SMILES Code : | O=C(O)CC(CC(O)=O)C(O)=O |
MDL No. : | MFCD00002723 |
InChI Key : | KQTIIICEAUMSDG-UHFFFAOYSA-N |
Pubchem ID : | 14925 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With pyridine; In m-xylene; at 140℃; | General procedure: Into a one-necked 25 mL flask, tricarballylic acid (518 mg, 2.95 mmol, 1.0 equiv) and the appropriate anhydride (8.83 mmol, 3 equiv) were suspended in m-xylene (5 mL, 0.6 M). Pyridine was added (47 muL, 0.59 mmol, 0.2 equiv) in one portion, then the mixture was heated to 140 C and stirred until the completion of the reaction was indicated by GC-MS (5-21 h). After cooling to r.t., CH2Cl2 (100 mL) was added and the mixture was passed through a short pad of Celite to remove insoluble side-products. The solution was washed with saturated Na2CO3 solution (2 10 mL) then with brine (10 mL). The organic phase was dried over Na2SO4, filtered, and evaporated to dryness. Purification by flash chromatography (hexanes/EtOAc) afforded the pure Fittig lactone. |