Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Diisopropyl Ether | HCID 7914 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | HCID 88600753 | HCID 88600753 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 88601107 | HCID 88601107 | 72.5% |
Reaction Steps
To a solution of benzhydryl 7-formamido-3-ethynyl-3-cephem-4-carboxylate (3 g) in a mixture of methanol (30 ml) and tetrahydrofuran (15 ml) was added phosphorus oxychloride (2.75 g) under ice-cooling. After the resultant mixture was stirred at room temperature for 30 minutes, the reaction mixture was added to diisopropyl ether (300 ml), and the precipitates were collected by filtration. The precipitates were added to a mixture of water (50 ml) and ethyl acetate (50 ml) under stirring, and the mixture was adjusted to pH 7.0 with saturated aqueous sodium bicarbonate. To the separated aqueous layer was added ethyl acetate (50 ml), and the mixture was acidified to pH 3.0 with 10% hydrochloric acid and the resultant precipitates were collected by filtration to give benzhydryl 7-amino-3-ethynyl-3-cephem-4-carboxylate (2.03 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04584290 |
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| Source dataset | uspto-grants-1986_04 |
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| ORD ID | ord-8e9058d666c8446ba0a21e11798f839b |
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| Source note | uspto-grants-1986_04 |
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