Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | 1-Hydroxybenzotriazole | HCID 75771 | — |
| Reactant | (Z)-2-(Trityloxyimino)-2-[2-(tritylamino)thiazol-4-yl]acetic Acid | HCID 10327150 | — |
| Reactant | 7beta-amino-3-[(1-amino-1H-tetrazol-4-yl)thiomethyl]-3-cephem-4-carboxylic acid | HCID 88675967 | — |
| 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 16162312 | HCID 16162312 | 41.6% |
Reaction Steps
A solution of 2-(2-tritylaminothiazol-4-yl)-(Z)-2-trityloxyiminoacetic acid (4.7 g, 7 mmol) (cf. Tetrahedron 1978, 34, 2233), 1-hydroxybenzotriazole (1.04 g, 7.7 mmol) and N,N'-dicyclohexylcarbodiimide (1.51 g, 7.35 mmol) in dimethylacetamide (27 ml) was allowed to react at room temperature for an hour. To the solution was added a solution of 7β-amino-3-[(1-amino-1H-tetrazol-4-yl)thiomethyl]-3-cephem-4-carboxylic acid (2.54 g, 7.7 mmol) and triethylamine (1.56 g, 15.4 mmol) in dimethylacetamide (20 ml) and water (0.5 ml) and the mixture was allowed to react at 5° C. for 1.5 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-trityloxyiminoacetamido]-3-[(1-amino-1H-tetrazol-5-yl)thiomethyl]-3-cephem-4-carboxylic acid (2.86 g, 41.6%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US04576938 |
|---|
| Source dataset | uspto-grants-1986_03 |
|---|
| ORD ID | ord-9e1af00b0cbf41d18cfa21b514d5e9c1 |
|---|
| Source note | uspto-grants-1986_03 |
|---|
