Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Acetone | HCID 180 | — |
| Reactant | Carbon Dioxide | HCID 280 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | Mitomycin A | HCID 19972 | — |
| Reactant | Tetrahydro-4H-pyran-4-ol | HCID 74956 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86744836 | HCID 86744836 | 21% |
Reaction Steps
A solution of mitomycin A (100 mg) in 2 ml of tetrahydro-4H-pyran-4-ol was stirred at room temperature and under nitrogen for 45 minutes with 500 mg of a 1.6% solution of KOH in tetrahydro-4H-pyran-4-ol. The reaction mixture was diluted with a little ether and then decomposed with dry ice. Additional ether was added and the solid that deposited (42 mg) was filtered off and discarded. The pink filtrate was concentrated under reduced pressure and the residue was isolated twice on a silica gel plate, using 20% of tetrahydrofuran in ether as a solvent in the first isolation and 15% of acetone in ether in the second isolation. This procedure gave 25 mg (21%) of the title compound, having a melting point of 115°-120° C. (decomposition) and providing the following analysis:
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05023253 |
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| Source dataset | uspto-grants-1991_06 |
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| ORD ID | ord-0999a066da23425396beb89790a1c9ce |
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| Source note | uspto-grants-1991_06 |
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