Ethanol → allyl [(3S,4S)-2-oxo-4-[(R)-3-oxo-1,4-dithian-2-yl]-3-[(R)-1-(trimethylsilyloxy)ethyl]azetidin-1-yl]glyoxylate

HRID 275283Notes

Reaction equation

HRID 275283 reaction equation
[CH3:1][Si:2]([CH3:19])([CH3:18])[O:3][C@@H:4]([C@@H:6]1[C@@H:9]([C@@H:10]2[C:15](=[O:16])[S:14][CH2:13][CH2:12][S:11]2)[NH:8][C:7]1=[O:17])[CH3:5].N1C=CC=CC=1.Cl[C:27](=[O:34])[C:28]([O:30][CH2:31][CH:32]=[CH2:33])=[O:29].C(O)C>ClCCl.CCOCC>[O:17]=[C:7]1[C@H:6]([C@H:4]([O:3][Si:2]([CH3:18])([CH3:1])[CH3:19])[CH3:5])[C@@H:9]([C@@H:10]2[C:15](=[O:16])[S:14][CH2:13][CH2:12][S:11]2)[N:8]1[C:27](=[O:34])[C:28]([O:30][CH2:31][CH:32]=[CH2:33])=[O:29]

Participants

7

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 3018516Allyl chlorooxoacetateHCID 15238317(3S,4S)-3-[(R)-1-(trimethylsilyloxy)-ethyl]-4-[(R)-3-oxo-1,4-dithian-2-yl]azetidin-2-one

Product 1

HCID 15238319allyl [(3S,4S)-2-oxo-4-[(R)-3-oxo-1,4-dithian-2-yl]-3-[(R)-1-(trimethylsilyloxy)ethyl]azetidin-1-yl]glyoxylateYield 97.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of (3S,4S)-3-[(R)-1-(trimethylsilyloxy)-ethyl]-4-[(R)-3-oxo-1,4-dithian-2-yl]azetidin-2-one (650 mg), prepared in Reference Example 14, in dichloromethane (10 ml) was cooled at 0° C. and a solution of pyridine (483 mg) in dichloromethane (2 ml) and a solution of allyl chloroglyoxylate (603 g) in dichloromethane (3 ml) were added. The mixture was stirred at the same temperature for 2 hours. To this mixture was added ethanol (187 mg) at 0° C. and the mixture was stirred for 10 minutes, after which ether (30 ml) was added. The organic layer was washed with water, saturated copper sulfate solution and saturated aqueous sodium chloride solution in the order mentioned and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure and the residue was purified by flash column chromatography (packing: silica gel; ethyl acetate-hexane=1:5). The procedure gave allyl [(3S,4S)-2-oxo-4-[ (R)-3-oxo-1,4-dithian-2-yl]-3-[(R)-1-(trimethylsilyloxy)ethyl]azetidin-1-yl]glyoxylate as a colorless oil (853 mg).

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. washThe organic layer was washed with water, saturated copper sulfate solution and saturated aqueous sodium chloride solution in the order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure
  5. customthe residue was purified by flash column chromatography (packing: silica gel; ethyl acetate-hexane=1:5)

Sources & evidence

ORD record
ord-54265b8eb2a34fb6ad56937c199dafbb
Source dataset
uspto-grants-1995_02
Patent number
US05393751

Reaction notes

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