HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phosphorus oxychloride → 4-Nitrobenzyl 7-[2-[2-(2,2,2-trifluoroacetamido)thiazol-4-yl]-2-(4-fluorobenzyloxyimino)acetamido]-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-(4-Fluorobenzyloxyimino)-2-[2-(2,2,2-trifluoroacetamido)thiazol-4-yl]acetic acid | HCID 53687167 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-Nitrobenzyl 7-[2-[2-(2,2,2-trifluoroacetamido)thiazol-4-yl]-2-(4-fluorobenzyloxyimino)acetamido]-3-cephem-4-carboxylate | HCID 131712358 | 91.8% |
Reaction Steps
A solution of 4-nitrobenzyl 7-amino-3-cephem-4-carboxylate (2.5 g.), bis(trimethylsilyl)acetamide (4.5 g.) and trimethylsilylacetamide (6.8 g.) in tetrahydrofuran (50 ml.) and a solution of 2-[2-(2,2,2-trifluoroacetamido)thiazole-4-yl]-2-(4-fluorobenzyloxyimino)acetic acid (syn isomer, 3.2 g.), phosphoryl chloride (15 g.) and N,N-dimethylformamide (0.7 g.) in ethyl acetate (32.8 ml.) were treated in a similar manner to that of Example 1-(1) to give 4-nitrobenzyl 7-[2-[2-(2,2,2-trifluoroacetamido)thiazol-4-yl]-2-(4-fluorobenzyloxyimino)acetamido]-3-cephem-4-carboxylate (syn isomer, 4.85 g.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04372952 |
| Source dataset | uspto-grants-1983_02 |
| ORD ID | ord-310788fb59a148ae8a5e7fbacd204c08 |
| Source note | uspto-grants-1983_02 |