Hydrochloric Acid → (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinone

HRID 231243Notes

Reaction equation

HRID 231243 reaction equation
[Si:1]([O:8][C@@H:9]([C@H:11]1[C@@H:14]([C:15]#[C:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[NH:13][C:12]1=[O:21])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O.Cl>ClCCl.O.C(OCC)(=O)C>[Si:1]([O:8][C@@H:9]([C@@H:11]1[C@@H:14]([C:15]#[C:16][Si:17]([CH3:18])([CH3:19])[CH3:20])[NH:13][C:12]1=[O:21])[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 57192380Cis-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinone

Product 1

HCID 14158531(3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinoneYield 87.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (3R,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinone (0.73 g) in dichloromethane (10 ml) was added triethylamine (1 ml). To the solution, trimethylsilyl trifluoromethanesulfonate (1.2 ml) was added at 5° C. and the mixture was stirred for 15 hours at ambient temperature. The reaction mixture was poured into a mixture of ethyl acetate (100 ml), 10% hydrochloric acid (10 ml) and water (100 ml). After stirring for 30 minutes at ambient temp., the organic layer was separated, washed successively with brine, aqueous solution of sodium bicarbonate and brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from n-hexane to give 0.64 g of (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-trimethylsilylethynyl-2-azetidinone.

Workup

  1. stirringAfter stirring for 30 minutes at ambient temp.
  2. customthe organic layer was separated
  3. washwashed successively with brine, aqueous solution of sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-8e499a662daf4008bd466c8f7e84c31f
Source dataset
uspto-grants-1989_07
Patent number
US04845210

Reaction notes

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