Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Iodomethyl pivalate | HCID 104401 | — |
| Reactant | HCID 141573516 | HCID 141573516 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 141559376 | HCID 141559376 | 68.4% |
Reaction Steps
Sodium 7-[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-(tetrahydrofuran-3-yl)thio-3-cephem-4-carboxylate (80 mg) (as obtained in Example 1) was dissolved in dimethylformamide (1.6 ml) and the solution was cooled to -20° C. The solution, after addition of iodomethyl pivalate (77 mg) thereto, was stirred at a temperature of -20° to -10° C. for 30 minutes (for the esterification reaciton), after which cold water (5 ml) was added to the reaction solution. The resulting mixture was extracted with ethyl acetate, and the organic layer separated was washed with an aqueous sodium chloride, dried over magnesium sulfate and concentrated under reduced pressure to leave a yellow oil. The oily residue was purified by a column chromatography on a silica gel column (15 g) with elution using ethyl acetate as eluent to collect fractions containing the titled compound. Concentration of the fractions so collected under reduced pressure gave the titled compound (65 mg; 68%) as white powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US05332731 |
|---|
| Source dataset | uspto-grants-1994_07 |
|---|
| ORD ID | ord-fcddaba97f23440eb491b5a6ee4a5be0 |
|---|
| Source note | uspto-grants-1994_07 |
|---|