m-Chloroperbenzoic acid → allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylsulfinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 1464729Notes

Reaction equation

HRID 1464729 reaction equation
[C:1]([Si:5]([CH3:27])([CH3:26])[O:6][C@@H:7]([C@H:9]1[C:15](=[O:16])[N:14]2[C@@H:10]1[C@@H:11]([CH3:25])[C:12]([S:23][CH3:24])=[C:13]2[C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[CH3:8])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:36])C=1>ClCCl>[Si:5]([O:6][C@@H:7]([C@H:9]1[C:15](=[O:16])[N:14]2[C@@H:10]1[C@@H:11]([CH3:25])[C:12]([S:23]([CH3:24])=[O:36])=[C:13]2[C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[CH3:8])([C:1]([CH3:3])([CH3:2])[CH3:4])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57185440allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Product 1

HCID 86747784allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylsulfinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of allyl (4R,5S,6S)-6-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-4-methyl-3-methylthio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (66 mg) in dichloromethane (1 ml) cooled to 0° C. was added meta-chloroperbenzoic acid (27.7 mg). The mixture was stirred for 10 minutes at the same temperature, washed with aqueous sodium bicarbonate solution and dried. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography to give allyl (4R,5S,6S)-6-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-methyl-3-methylsulfinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (64 mg).

Workup

  1. washwashed with aqueous sodium bicarbonate solution
  2. customdried
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c458f5424a0c4cec84a7eb68dd375fce
Source dataset
uspto-grants-1994_04
Patent number
US05306816

Reaction notes

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