Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Morpholine | HCID 8083 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride | HCID 2723939 | — |
| Reactant | HCID 131722163 | HCID 131722163 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 131722178 | HCID 131722178 | 26.5% |
Reaction Steps
To a solution of benzhydryl 7β-(2-phenylacetamido)-3-(4-carboxymethylthiazol-2-yl)thio-3-cephem-4-carboxylate (500 mg) in N,N-dimethylformamide (10 ml) were added 1-hydroxybenzotriazole (123 mg), WSC.HCl (175 mg) and morpholine (79 mg) at room temperature. After stirring at room temperature for 2.5 hours, the solution was poured into a mixture of water and ethyl acetate, and adjusted to pH 7.0 with aqueous sodium hydrogen carbonate. The separated organic layer was washed with saturated sodium chloride solution (×3), dried over magnesium sulfate and evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel (eluent: ethyl acetate/n-hexane) to give benzhydryl 7β-(2-phenylacetamido)-3-(4-morpholinocarbonylmethylthiazol-2-yl)thio-3-cephem-4-carboxylate (147 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06150351 |
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| Source dataset | uspto-grants-2000_11 |
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| ORD ID | ord-05ae2b34b662431e9cd7bdf3b79d4ce5 |
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| Source note | uspto-grants-2000_11 |
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