Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Phosphorus pentachloride | HCID 24819 | — |
| Reactant | Benzhydryl 7-(5-benzamido-5-benzhydryloxycarbonylpentanamido)-3-hydroxymethyl-3-cephem-4-carboxylate | HCID 12817988 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 12817992 | HCID 12817992 | 112.4% |
Reaction Steps
To a solution of benzhydryl 7-(5-benzamido-5-benzhydryloxycarbonylpentanamido)-3-hydroxymethyl-3-cephem-4-carboxylate (100 g) in methylene chloride (600 ml) was added at a time phosphorus pentachloride (25.6 g) at -30° C., followed by adding dropwise pyridine (9.8 g) at the same temperature. After the reaction mixture was stirred at -20° C. for an hour, it was poured into a mixture of methylene chloride (500 ml) and water (300 ml). The separated organic layer was washed with an aqueous sodium chloride, dried over magnesium sulfate and then evaporated to dryness to obtain benzhydryl 7-(5-benzamido-5-benzhydryloxycarbonylpentanamido)-3-chloromethyl-3-cephem-4-carboxylate (114.5 g), mp 90°-110° C. (dec.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04423213 |
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| Source dataset | uspto-grants-1983_12 |
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| ORD ID | ord-567d1a794e9042c599ee2d2bbe9cda7a |
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| Source note | uspto-grants-1983_12 |
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