HuagongsheHuagongshe Chemistry Print Report · For research reference only
Pyridine → (3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-(benzylthiocarbonyl)ethyl]-2-azetidinone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Pyridine | HCID 1049 | — |
| Reactant | Benzyl mercaptan | HCID 7509 | — |
| Reactant | (R)-2-[(3S,4S)-3-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionic acid | HCID 9882831 | — |
| Reactant | 1H-Imidazolium, 2-chloro-4,5-dihydro-1,3-dimethyl-, chloride | HCID 10986715 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | (3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-(benzylthiocarbonyl)ethyl]-2-azetidinone | HCID 57101236 | 67.2% |
Reaction Steps
(3S ,4S)-3-[(1R)-1-t-Butyldimethylsilyloxyethyl]-4-[(1R)-1-carboxyethyl]-2-azetidinone (995 mg, 3.3 mmol), benzylmercaptan (409 mg, 3.5 mmol) and 2-chloro-1,3-dimethylimidazolinium chloride (592 mg, 3.5 mmol) are dissolved in methylene chloride (3 ml), and thereto is added dropwise pyridine (550 mg, 7.0 mmol) under ice-cooling. The mixture is stirred at room temperature for 10 hours. The reaction solution is treated in the same manner as in Reference Example 3 to give (3S,4S)-3-[(1R)-1-t-butyldimethylsilyloxyethyl]-4-[(1R)-1-(benzylthiocarbonyl)ethyl]-2-azetidinone (868 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05578722 |
| Source dataset | uspto-grants-1996_11 |
| ORD ID | ord-a131b896cdf74374bbfebc47c9b0286f |
| Source note | uspto-grants-1996_11 |