Water → HCID 57286878, compound

Participants

Reaction Steps

To a solution of (3S,4S)-3-[(1R)-1-hydroxyethyl]-4-[(1R)-1-phenylthiocarbonylethyl]-1-allyloxycarbonylmethyl-2-azetidinone (5.04 g: 13.35 mmole) in toluene (40 ml) under ice cooling, pyridine (1.51 ml: 18.69 mmole) is added and trimethylchlorosilane (2.26 ml: 17.36 mmole) is added dropwise. The mixture is stirred at room temperature for 1.5 hours. Water (80 ml) is added to the reaction mixture, and aqueous layer is extracted with toluene. The extract and the organic layer are combined, washed with water (2 times) and saturated brine, dried over magnesium sulfate, and concentrated in vacuo to give crude (3S,4S)-3-[(1R)-1-trimethylsilyloxyethyl]-4-[(1R)-1-phenylthiocarbonylethyl]-1-allyloxycarbonylmethyl-2-azetidinone (5.614 g) as oily residue. Yield: 94%.

Provenance & Evidence