HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → (6R)-3-[[2-[(2-aminoacetyl)amino]-[1,3]thiazolo[4,5-c]pyridin-5-ium-5-yl]methyl]-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | benzhydryl (6R)-3-(iodomethyl)-7-[[(2Z)-2-methoxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | HCID 13239634 | — |
| Reactant | 2-(N-t-Butoxycarbonylglycylamino)thiazolo[4,5-c]pyridine | HCID 15593546 | — |
| Catalyst | Anisole | HCID 7519 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | (6R)-3-[[2-[(2-aminoacetyl)amino]-[1,3]thiazolo[4,5-c]pyridin-5-ium-5-yl]methyl]-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | HCID 177727401 | 96% |
Reaction Steps
A mixture of diphenylmethyl 7-[(Z)-2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-iodomethyl-3-cephem-4-carboxylate [VIIa] (237 mg, 0.29 mmole) and 2-(N-t-butoxycarbonylglycylamino)thiazolo[4,5-c]pyridine (95 mg, 0.31 mmole) in 2 ml of dry DMSO was allowed to stand at room temperature for 2 hours and then diluted with ether to give the crude quaternary salt, which was treated with 90% TFA and 2 drops of anisole at room temperature for 30 minutes. The mixture was evaporated and triturated with ether to afford 168 mg of pale yellow precipitate, which was purified by a column of HP-20 resin (40 ml) using 30% aqueous CH3OH as an eluant to give 88 mg of the title product Iq. Mp. 178°-187° C. (dec.). Estimated purity by HPLC: 60%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04500526 |
| Source dataset | uspto-grants-1985_02 |
| ORD ID | ord-b56af48724d74febaa9500672fbe51d4 |
| Source note | uspto-grants-1985_02 |