HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phosphorus oxychloride → 4-Nitrobenzyl 7-[2-(2-aminothiazol-4-yl)-2-benzyloxyiminoacetamido]-3-cephem-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | Acetamide, 2-(trimethylsilyl)- | HCID 357676 | — |
| Reactant | p-Nitrobenzyl 7-amino-3-cephem-4-carboxylate | HCID 12775080 | — |
| Reactant | 2-(2-Aminothiazol-4-yl)-2-benzyloxyiminoacetic acid | HCID 54172563 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-Nitrobenzyl 7-[2-(2-aminothiazol-4-yl)-2-benzyloxyiminoacetamido]-3-cephem-4-carboxylate | HCID 131712332 | 48% |
Reaction Steps
A solution of 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (3.35 g.) and trimethylsilylacetamide (9.2 g.) in ethyl acetate (50 ml.) and a solution of 2-(2-aminothiazol-4-yl)-2-benzyloxyiminoacetic acid (syn isomer, 2.77 g.), trimethylsilylacetamide (0.9 g.), N,N-dimethylformamide (0.9 g.) and phosphoryl chloride (3.84 g.) in tetrahydrofuran (30 ml.) were treated in a similar manner to that of Example 4 to give 4-nitrobenzyl 7-[2-(2-aminothiazol-4-yl)-2-benzyloxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 2.85 g.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04284631 |
| Source dataset | uspto-grants-1981_08 |
| ORD ID | ord-93c1dd746bd649169cc65d5cb4e383c1 |
| Source note | uspto-grants-1981_08 |