HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → O-benzhydryl (6R)-3-(1,3-benzothiazol-2-yl)-8-oxo-7-[[(2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbothioate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Phosphorus oxychloride | HCID 24813 | — |
| Reactant | (Z)-2-(Trityloxyimino)-2-[2-(tritylamino)thiazol-4-yl]acetic Acid | HCID 10327150 | — |
| Reactant | Diphenylmethyl 7-amino-3-(benzothiazol-2-yl)thio-3-cephem-4-carboxylate | HCID 131719158 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | O-benzhydryl (6R)-3-(1,3-benzothiazol-2-yl)-8-oxo-7-[[(2Z)-2-[2-(tritylamino)-1,3-thiazol-4-yl]-2-trityloxyiminoacetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carbothioate | HCID 141562819 | 73% |
Reaction Steps
350 mg of diphenylmethyl 7-amino-3-(benzothiazol-2-yl)thio-3-cephem-4-carboxylate as synthesized in the same manner as in Example 1 (b) above were dissolved in ml of methylene chloride, and to the solution obtained were added 531 mg of (Z)-2-(2-tritylaminothiazol-4-yl)-trityloxyiminoacetic acid, 0.21 ml of pyridine and 74 μl of phosphorus oxychloride. Next, the acylation reaction and the post-treatment of the reaction solution were carried out in the same way as in Example 1 (b), and the resultant residue was then purified by a column chromatography on 35 g of silica gel (as developed with mixed solvents of toluene and ethyl acetate, 10:1) to obtain 566 mg of the titled compound (yield, 73%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05461044 |
| Source dataset | uspto-grants-1995_10 |
| ORD ID | ord-681a6c069bac4c7ba6bc76fd2db916a2 |
| Source note | uspto-grants-1995_10 |