Chlorotrimethylsilane → (3R,4R)-3-[(1R)-1-t-Butyldimethylsilyloxyethyl]-4-acetoxy-1-trimethylsilyl-2-azetidinone
Reaction equation
[C:1]([O:4][C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH3:11])(=[O:3])[CH3:2].C(N(CC)CC)C.[CH3:27][Si:28]([CH3:31])([CH3:30])Cl>O1CCCC1>[C:1]([O:4][C@H:5]1[N:8]([Si:28]([CH3:31])([CH3:30])[CH3:27])[C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][Si:13]([C:16]([CH3:18])([CH3:17])[CH3:19])([CH3:14])[CH3:15])[CH3:11])(=[O:3])[CH3:2]Participants
Procedure
To an ice-cooled solution of 50g (0.174 mole) of (3R, 4R)-4-acetoxy-3-[(R)-1-t-butyldimethylsilyloxyethyl]-2 -azetidinone and 24.69 (0.244 mole) of triethylamine in 500 ml of tetrahydrofuran were added 26.5g (0.244 mole) of trimethylchlorosilane under a nitrogen stream. The reaction temperature was allowed to rise to room temperature and the reaction mixture was stirred for 2 hours. The precipitate was filtered off using a Celite (trade mark) filter aid. After the precipitate had been washed with ether twice, the filtrate and the washings were combined, and the solvent was evaporated. The residue was washed with ether to filter off the insoluble materials, Evaporation of the solvent from the filtrate gave 6.23 g (yield 100%) of the title compound as a semi-solid.
Workup
- customto rise to room temperature
- filtrationThe precipitate was filtered off
- filtrationfilter aid
- washAfter the precipitate had been washed with ether twice
- customthe solvent was evaporated
- washThe residue was washed with ether
- filtrationto filter off
- customthe insoluble materials, Evaporation of the solvent from the filtrate
Sources & evidence
- ORD record
- ord-47aab2b7d5e5450b9753090c2da93fc8
- Source dataset
- uspto-grants-1999_01
- Patent number
- US05856556
Reaction notes
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