Dimethyl Sulfide → (3R,4R)-4-Acetoxy-3-((R)-(tert-butyldimethylsilyloxy)ethyl)-2-azetidinone

HRID 231240Notes

Reaction equation

HRID 231240 reaction equation
ClC1C=CC=[C:4]([C:8](OO)=[O:9])C=1.C([C@H:15]1[NH:18][C:17](=[O:19])[C@H:16]1[C@H:20]([O:22][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH3:21])(=O)C.C(=O)([O-])[OH:31].[Na+].CSC>C(OCC)(=O)C>[C:8]([O:19][C@H:17]1[NH:18][C:15](=[O:31])[C@H:16]1[C@H:20]([O:22][Si:23]([C:26]([CH3:27])([CH3:28])[CH3:29])([CH3:24])[CH3:25])[CH3:21])(=[O:9])[CH3:4]

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 57147100(3R,4S)-4-acetyl-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]2-azetidinone

Product 1

HCID 13073890(3R,4R)-4-Acetoxy-3-((R)-(tert-butyldimethylsilyloxy)ethyl)-2-azetidinone

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

m-Chloroperbenzoic acid (0.5 g) is added to a solution of the object compound of Example 22 (0.08g) in ethyl acetate (8 ml), and the mixture is stirred at room temperature for 3 days and then poured into a mixture of ethyl acetate (50 ml), aqueous sodium hydrogen carbonate (20 ml) and dimethyl sulfide (0.4 ml). The mixture is stirred at room temperature for 30 minutes. The organic layer is separated, washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue is subjected to silica gel column chromatography (eluent: 15% ethyl acetate-85% hexane) to give 0.045 g of (3S,4R)-4-acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-2-azetidinone.

Workup

  1. stirringThe mixture is stirred at room temperature for 30 minutes
  2. customThe organic layer is separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-295a58d7d27a4aad9f5d6f9e24a55e1f
Source dataset
uspto-grants-1989_07
Patent number
US04845210

Reaction notes

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