HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-[4-methoxyphenoxymethylthio)-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | (4-Methoxyphenoxy)acetyl chloride | HCID 3126949 | — |
| Reactant | 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester | HCID 14084562 | — |
| Catalyst | 4-(Dimethylamino)pyridine | HCID 14284 | — |
| Catalyst | Silver | HCID 23954 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-[4-methoxyphenoxymethylthio)-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester | HCID 86744307 | — |
Reaction Steps
The starting material is prepared as follows: A solution of 2.43 g of the silver salt of 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester in 40 ml of absolute dichloromethane is treated successively with 0.56 ml of pyridine, 20 mg of 4-dimethylaminopyridine and 1.12 g of 4-methoxyphenoxyacetylchloride. The work-up procedure described above gives the desired 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-[4-methoxyphenoxymethylthio)-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04965260 |
| Source dataset | uspto-grants-1990_10 |
| ORD ID | ord-4269d1c678884a69b854ea41f7b3e130 |
| Source note | uspto-grants-1990_10 |