Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | N-{2-[(Diphenylmethoxy)carbonyl]-3-(morpholin-4-yl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-7-yl}-2-phenoxyethanimidic acid | HCID 44151031 | — |
| Solvent | Acetic Acid | HCID 176 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 13892058 | HCID 13892058 | — |
Reaction Steps
A solution of 1.05 g of sodium cyanoborohydride in 30 ml of tetrahydrofurane is added dropwise over 20 minutes to a solution of 5.86 g (10 mmols) of 7β-phenoxyacetylamino-3-morpholino-3-cephem-4-carboxylic acid benzhydryl ester in 50 ml of methylene chloride and 50 ml of glacial acetic acid, whereupon vigorous evolution of gas occurs. Then 20 ml of formic acid are added and the reaction mixture is stirred for 16 hours at room temperature. For working up, the reaction mixture is diluted with 300 ml of methylene chloride and the organic phase is washed four times with 100 ml of water, then dried over sodium sulfate. The solvent is distilled off in vacuo. The almost colourless crude product is chromatographed on silica gel with toluene/ethyl acetate (9:1), affording pure 7β-phenoxyacetylamino-3-cephem-4-carboxylic acid benzhydryl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04436903 |
|---|
| Source dataset | uspto-grants-1984_03 |
|---|
| ORD ID | ord-faf854d518c84ecfac27c7f67d928302 |
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| Source note | uspto-grants-1984_03 |
|---|
