HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Dimethylaminopyridine → 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-(4-allyloxycarbonylaminophenoxyacetylthio)-2-oxoazetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Dimethylaminopyridine | HCID 21885 | — |
| Reactant | 1-Chloro-N,N-2-trimethylpropenylamine | HCID 640792 | — |
| Reactant | 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-mercapto-2-oxo-azetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester | HCID 14084562 | — |
| Reactant | 2-(4-{[(Prop-2-en-1-yloxy)carbonyl]amino}phenoxy)acetic acid | HCID 22160445 | — |
| Catalyst | Silver | HCID 23954 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 2-[(3S,4R)-3-[(1R)-1-allyloxycarbonyloxyethyl]-4-(4-allyloxycarbonylaminophenoxyacetylthio)-2-oxoazetidin-1-yl]-2-triphenylphosphoranylideneacetic acid allyl ester | HCID 57095775 | — |
Reaction Steps
1 g of 4-(allyloxycarbonylamino)-phenoxyacetic acid is suspended in 2 ml of CH2Cl2 and 0.6 ml of 1-chloro-1-dimethylamino-2-methylprop-1-ene is added thereto. The mixture is stirred for 75 minutes and is then added dropwise, over a period of 5 minutes, to a solution of 1.74 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, 50 mg of dimethylaminopyridine and 0.41 ml of pyridine in 30 ml of absolute methylene chloride. The title compound is obtained after working up analogously to Example 1.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04965260 |
| Source dataset | uspto-grants-1990_10 |
| ORD ID | ord-1d8f7f00493542e1ba237657de13eb2b |
| Source note | uspto-grants-1990_10 |