Hydrochloric Acid → (3S,4S)-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone
Reaction equation
FC(F)(F)S(O[Si](C)(C)C)(=O)=O.[OH:13][C@@H:14]([C@H:16]1[C@@H:19]([C:20]#[C:21][Si:22]([CH3:25])([CH3:24])[CH3:23])[NH:18][C:17]1=[O:26])[CH3:15].C(N(CC)CC)C.Cl>O.C(O)C.C(OCC)(=O)C.ClCCl>[OH:13][C@@H:14]([C@@H:16]1[C@@H:19]([C:20]#[C:21][Si:22]([CH3:23])([CH3:25])[CH3:24])[NH:18][C:17]1=[O:26])[CH3:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Procedure
Trimethylsilyl trifluoromethanesulfonate (0.48 ml) was added to a mixture of (3R,4S)-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone (0.15 g), triethylamine (0.4 ml) and dichloromethane (7 ml) at 5° C. The mixture was stirred at ambient temperature for 3 hours and poured into a mixture of ethyl acetate (70 ml), ethanol (10 ml), 10% hydrochloric acid (10 ml) and water (50 ml). After stirring for 30 min. at ambient temp., the organic layer was separated, washed successively with brine, saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated under reduced pressure. The precipitates were recrystallized from n-hexane to give 0.13 g of (3S,4S)-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone.
Workup
- stirringAfter stirring for 30 min. at ambient temp.
- customthe organic layer was separated
- washwashed successively with brine, saturated aqueous sodium bicarbonate and brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe precipitates were recrystallized from n-hexane
Sources & evidence
- ORD record
- ord-62a7132377fb40db9de037c2fc5349fa
- Source dataset
- uspto-grants-1989_07
- Patent number
- US04845210
Reaction notes
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