HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phosphorus oxychloride → 4-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)-acetamido]-3-chloro-3-cephem-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | Acetamide, 2-(trimethylsilyl)- | HCID 357676 | — |
| Reactant | 2-(2,2,2-Trifluoroethoxyimino)-2-(2-formylaminothiazol-4-yl)acetic acid | HCID 54018458 | — |
| Reactant | 4-Nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride | HCID 70362150 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)-acetamido]-3-chloro-3-cephem-4-carboxylate | HCID 131712486 | 96.7% |
Reaction Steps
A solution of 2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetic acid (syn isomer, 0.9 g.), N,N-dimethylformamide (0.24 g.) and phosphoryl chloride (0.5 g.) in ethyl acetate (10 ml.) and a solution of 4-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride (1.23 g.) and trimethylsilylacetamide (2.8 g.) in ethyl acetate (20 ml.) were treated in a similar manner to that of Example 21-(1) to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 1.9 g.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04399133 |
| Source dataset | uspto-grants-1983_08 |
| ORD ID | ord-49581bff4e1143c8957059501a9a4880 |
| Source note | uspto-grants-1983_08 |