HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phosphorus oxychloride → 7-[2-(2-Formamido-5-bromothiazol-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-bromothiazol-4-yl)-2-methoxyiminoacetic acid | HCID 53801102 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 7-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid | HCID 131715338 | 59.6% |
Reaction Steps
A solution of 7-amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer, 1.1 g.) and trimethylsilylacetamide (3.4 g.) in dry ethyl acetate (30 ml.) and a mixture of dimethylformamide (0.3 ml.), phosphoryl chloride (0.35 ml.), 2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetic acid (syn isomer, 1.0 g.) and dry ethyl acetate (30 ml.) were treated in a similar manner to that of Example 1-(1) to give 7-[2-(2-formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer, 1.2 g.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04703046 |
| Source dataset | uspto-grants-1987_10 |
| ORD ID | ord-8b709a4d5a5547869888ecf39d0398b4 |
| Source note | uspto-grants-1987_10 |