HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phosphorus oxychloride → 4-Nitrobenzyl 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | Acetamide, 2-(trimethylsilyl)- | HCID 357676 | — |
| Reactant | Bistrimethylsilylacetamid | HCID 11708267 | — |
| Reactant | p-Nitrobenzyl 7-amino-3-cephem-4-carboxylate | HCID 12775080 | — |
| Reactant | 2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acid | HCID 53801102 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Isopropanol | HCID 3776 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-Nitrobenzyl 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate | HCID 131715359 | 43.1% |
Reaction Steps
A solution of 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (3.3 g.), trimethylsilylacetamide (6.4 g.) and bis(trimethylsilyl)acetamide (6.0 g.) in dry ethyl acetate (100 ml.) and a solution of dimethylformamide (0.9 ml.), phosphoryl chloride (1.1 ml.) and 2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 5.1 g.) in dry ethyl acetate (5 ml.) were treated in a similar manner to that of Example 1-(1) (isopropyl alcohol was used for pulverization instead of diethyl ether) to give 4-nitrobenzyl 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 2.65 g.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04703046 |
| Source dataset | uspto-grants-1987_10 |
| ORD ID | ord-6497734417d3470aae8799026e4ae1aa |
| Source note | uspto-grants-1987_10 |