Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Iodomethyl pivalate | HCID 104401 | — |
| Reactant | 1,5-Diazabicyclo(5,4,0)undec-5-ene | HCID 314112 | — |
| Reactant | HCID 131716544 | HCID 131716544 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 131716560 | HCID 131716560 | 47.4% |
Reaction Steps
In 80 ml of acetone was suspended 16.9 g of 7-amino-3-[(2-methoxymethyl-5-methyl-s-triazolo[1,5-a]pyrimidin-7yl)thiomethyl]-3-cephem-4-carboxylic acid and ice-cooled, and then 5.98 ml of 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU) was added dropwise to the solution and the mixture was stirred for 30 minutes. After 9.68 g of pivaloyloxymethyl iodide was added dropwise to the mixture, the mixture was stirred at room temperature for 20 minutes. After the reaction mixture was poured into a mixed solution of 280 ml of ethyl acetate and 200 ml of water and stirred, an organic layer was separated therefrom, washed with water, further washed with a saturated saline solution and dried over anhydrous magnesium sulfate. By removing a solvent, an oily product was obtained. This oily product was purified through silica gel column chromatography. To the oily product obtained was added ether to powderize, and it was collected by filtration and dried to obtain 10.17 g of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04956462 |
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| Source dataset | uspto-grants-1990_09 |
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| ORD ID | ord-b93fe695a5c649cdb2d9720beaf6cbaf |
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| Source note | uspto-grants-1990_09 |
|---|