HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 4-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | 2-Hexyloxyimino-2-(2-formylaminothiazol-4-yl)acetic acid | HCID 54520824 | — |
| Reactant | 4-Nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride | HCID 70362150 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-Nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate | HCID 131712498 | 90.2% |
Reaction Steps
A solution of 2-(2-formamidothiazol-4-yl)-2-n-hexyloxyiminoacetic acid (syn isomer, 3.24 g.), N,N-dimethylformamide (0.951 g.), and phosphoryl chloride (2.00 g.) in ethyl acetate (20 ml.), and a solution of 4-nitrobenzyl 7-amino-3-chloro-3-cephem-4-carboxylate hydrochloride (4 g.) in a mixture of acetone (20 ml.), water (20 ml.) and tetrahydrofuran (40 ml.) were treated in a similar manner to that of Example 21-(1) to give 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-hexyloxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 5.78 g.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04400379 |
| Source dataset | uspto-grants-1983_08 |
| ORD ID | ord-94dcb63d36fd40adb7bbc7d9a53f8183 |
| Source note | uspto-grants-1983_08 |