Dimethyl Sulfide → HCID 131714932, compound

HRID 414741Notes

Reaction equation

HRID 414741 reaction equation
COC(=O)C([N:8]1[C@H:11]([S:12]([CH3:15])(=[O:14])=[O:13])[C@@H:10]([C:16]([CH3:24])([CH3:23])[O:17][SiH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:9]1=[O:25])=C(C)C.O=[O+][O-].O=O.CSC>C(Cl)Cl>[C:19]([SiH2:18][O:17][C:16]([CH3:24])([CH3:23])[C@@H:10]1[C@@H:11]([S:12]([CH3:15])(=[O:14])=[O:13])[NH:8][C:9]1=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 131711318Oxygen ozoneHCID 131714933HCID 131714933, compound

Product 1

HCID 131714932HCID 131714932, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 25 g (61.7 mmol) of 2-[(3S,4R)-3-(tert.-butyl-dimethyl-silyloxymethyl)-4-methylsulphonyl-2-oxoazetidin-1-yl]-3-methyl-2-butenoic acid methyl ester in 400 ml of methylene chloride is treated at -10° with an ozone/oxygen mixture. The disappearance of the starting material is monitored by thin layer chromatography. When the reaction is complete, 30 ml of dimethyl sulphide are added and the mixture is stirred for a further 3 hours at room temperature. The solution is concentrated and the residue is taken up in a mixture of 160 ml of methanol, 24 ml of ethyl acetate and 3 ml of water and heated for 40 minutes at 70° C. The solvent is then removed and the residue is evaporated twice in the presence of toluene. The crystallising oil is taken up in methylene chloride and the crystals, consisting of (3S,4R)-3-hydroxymethyl-4-methylsulphonylazetidin-2-one, are isolated by filtration. The filtrate is concentrated and (3S,4R)- 3-(tert.-butyl-dimethyl-silyloxymethyl)-4-methylsulphonylazetidin-2-one is obtained in pure form by chromatography over silica gel with toluene/ethyl acetate (3:1):

Workup

  1. concentrationThe solution is concentrated
  2. additionthe residue is taken up in a mixture of 160 ml of methanol, 24 ml of ethyl acetate and 3 ml of water
  3. temperatureheated for 40 minutes at 70° C
  4. customThe solvent is then removed
  5. customthe residue is evaporated twice in the presence of toluene
  6. customare isolated by filtration
  7. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-e9a1e4ca04744c51a575253e666f6049
Source dataset
uspto-grants-1988_12
Patent number
US04794109

Reaction notes

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