HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → 7-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-n-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | 2-(2-Formamidothiazol-4-yl)-2-carbamoylmethoxyiminoacetic acid | HCID 53805230 | — |
| Reactant | 7-amino-3-(1-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid | HCID 70432331 | — |
| Solvent | Acetone | HCID 180 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 7-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-n-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid | HCID 131715301 | 38.6% |
Reaction Steps
A solution of 2-(2-formamidothiazol-4-yl)-2-carbamoylmethoxyiminoacetic acid (syn isomer, 1.35 g.), N,N-dimethylformamide (0.814 g.) and phosphoryl chloride (1.71 g.) in tetrahydrofuran (13.4 ml.) and a solution of 7-amino-3-(1-n-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (1.95 g.) in 50% aqueous acetone (20 ml.) were treated in a similar manner to that of Example 9-(1) to give 7-[2-(2-formamidothiazol-4-yl)-2-cyanomethoxyiminoacetamido]-3-(1-n-hexyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 1.2 g.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04698337 |
| Source dataset | uspto-grants-1987_10 |
| ORD ID | ord-fb2ffc85d74741899de2c0eb88226271 |
| Source note | uspto-grants-1987_10 |