HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phosphorus oxychloride → 7-[2-(2-Formamido-5-chlorothiazol-4-yl)-2-methoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | Acetamide, 2-(trimethylsilyl)- | HCID 357676 | — |
| Reactant | 7-Amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3cephem-4-carboxylic acid | HCID 12889187 | — |
| Reactant | 2-(2-Formamido-5-chlorothiazol-4-yl)-2-methoxyiminoacetic acid | HCID 53874775 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 7-[2-(2-Formamido-5-chlorothiazol-4-yl)-2-methoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid | HCID 131715353 | 98.6% |
Reaction Steps
A solution of 7-amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (4.3 g.) and trimethylsilylacetamide (17.1 g.) in dry ethyl acetate (130 ml.) and a solution of dimethylformamide (0.92 ml.), phosphoryl chloride (1.09 ml.) and 2-(2-formamido-5-chlorothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 2.6 g.) in dry ethyl acetate (27 ml.) were treated in a similar manner to that of Example 1-(1) to give 7-[2-(2-formamido-5-chlorothiazol-4-yl)-2-methoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer, 5.6 g.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04703046 |
| Source dataset | uspto-grants-1987_10 |
| ORD ID | ord-58a6493a6f6743d1a90e645d1727ab24 |
| Source note | uspto-grants-1987_10 |