HuagongsheHuagongshe Chemistry Print Report · For research reference only
(4-methoxyphenyl)methyl (6R)-7-[[(2Z)-2-[(2S)-1-benzhydryloxy-1-oxopropan-2-yl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate → (4-methoxyphenyl)methyl (6R)-7-[[(2Z)-2-[(2S)-1-benzhydryloxy-1-oxopropan-2-yl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-3-([1,3]thiazolo[4,5-b]pyridin-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (4-methoxyphenyl)methyl (6R)-7-[[(2Z)-2-[(2S)-1-benzhydryloxy-1-oxopropan-2-yl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-(chloromethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | HCID 88420502 | — |
| Reactant | Thiazolo[4,5-c]pyridine-2-thiol | HCID 178527814 | — |
| Reactant | HCID 178527821 | HCID 178527821 | — |
| Product | (4-methoxyphenyl)methyl (6R)-7-[[(2Z)-2-[(2S)-1-benzhydryloxy-1-oxopropan-2-yl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-8-oxo-3-([1,3]thiazolo[4,5-b]pyridin-2-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | HCID 141566707 | 62.4% |
Reaction Steps
Using 305 mg of p-methoxybenzyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-{(S)-1-diphenylmethoxycarbonylethoxyimino}acetamido]-3-chloromethyl-3-cephem-4-carboxylate and 60 mg of 2-mercaptothiazolo[4,5-b]pyridine in place of p-methoxybenzyl 7-{(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido}-3-chloromethyl-3-cephem-4-carboxylate and 2-mercaptothiazolo[4,5-c]pyridine, respectively, the reaction and purification were carried out in the same manner as in Example 1(a) to obtain 215 mg of the title compound in a yield of 62%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05464829 |
| Source dataset | uspto-grants-1995_11 |
| ORD ID | ord-e560f6da7c3b4636b7b5af0fda36b982 |
| Source note | uspto-grants-1995_11 |