Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | (2Z)-2-(2-amino-2-oxoethoxy)imino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid | HCID 12816813 | — |
| Reactant | 7beta-amino-3-(1-amino-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid | HCID 13367510 | — |
| Reactant | (6R,7R)-3-[(1-aminotetrazol-5-yl)sulfanylmethyl]-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-butoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | HCID 178454536 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylacetamide | HCID 31374 | — |
| Product | HCID 178514051 | HCID 178514051 | 69.3% |
Reaction Steps
A solution of 2-(2-tritylaminothiazol-4-yl)-(Z)-2-carbamoylmethoxyiminoacetic acid (3.02 g, 6.2 mmol), 1-hydroxybenzotriazole (0.900 g, 6.7 mmol) and N,N'-dicyclohexylcarbodiimide (1.38 g, 6.7 mmol) in dimethylacetamide (17 ml) was stirred at 0°-5° C. for an hour. To the solution was added a solution of 7β-amino-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (2.38 g, 7.2 mmol) and triethylamine (1.60 g, 15.8 mmol) in dimethylacetamide (12 ml) and water (2 ml) at the same temperature and allowed to react for 2 hours. Then the mixture was treated in a manner similar to that described in Example 6, (c) to give pale yellow powder of 7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-carbamoylmethoxyiminoacetamido]-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (3.43 g, 69.3%), mp~115° C. (decomposition).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04576938 |
|---|
| Source dataset | uspto-grants-1986_03 |
|---|
| ORD ID | ord-2c4d00ff31164fffb2b8ec94f31ce57d |
|---|
| Source note | uspto-grants-1986_03 |
|---|
