HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phosphorus oxychloride → 7-[2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid
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 | 7-amino-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid | HCID 70432653 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 7-[2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid | HCID 131715312 | 39.5% |
Reaction Steps
A solution of 2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetic acid (syn isomer, 1.5 g.), N,N-dimethylformamide (0.40 g.) and phosphoryl chloride (0.84 g.) in ethyl acetate (15 ml.) and a solution of 7-amino-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (1.77 g.) and trimethylsilylacetamide (3.93 g.) in ethyl acetate (25 ml.) were treated in a similar manner to that of Example 17 (1) to give 7-[2-(2-formamidothiazol-4-yl)-2-(2,2,2-trifluoroethoxyimino)acetamido]-3-(1-allyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer, 1.25 g.).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04698337 |
| Source dataset | uspto-grants-1987_10 |
| ORD ID | ord-81cd9de6cb064f53b055fe10c049bc81 |
| Source note | uspto-grants-1987_10 |