Dimethyl Sulfide → HCID 18611327, compound

HRID 2413884Notes

Reaction equation

HRID 2413884 reaction equation
O=[O+][O-].[C:4]([O:7][CH:8]1[N:11](C(=C(C)C)C(O)=O)[C:10](=[O:19])[C@@H:9]1[C@H:20]([F:22])[CH3:21])(=[O:6])[CH3:5].CSC>>[C:4]([O:7][CH:8]1[NH:11][C:10](=[O:19])[C@@H:9]1[C@H:20]([F:22])[CH3:21])(=[O:6])[CH3:5]

Participants

4

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823Ozone2×HCID 131715436HCID 131715436, compound

Product 1

HCID 18611327HCID 18611327, compound

Procedure

Ozone is passed through a solution of 6.2 g of 2-[4-acetoxy-(3R)-3-[1(R)-fluorethyl]-2-oxoazetidine-1-yl]-3-methyl-2-butenoic acid.benzhydrylester at -78° until a permanent blue colour is achieved. The excess ozone is drive out with nitrogen and 1.75 g of dimethylsulphide added. The reaction mixture is allowed to rise to room temperature. The solvent is evaporated on a rotary evaporator, the residue taken up in 100 ml of methanol and after addition of 2 drops of triethylamine stirred for 2 hours. After renewed concentration the residue is chromatographed on silica gel (dichloromethane/ethylacetate=10/3) to obtain the oily title compound.

Workup

  1. customat -78°
  2. additionadded
  3. customto rise to room temperature
  4. customThe solvent is evaporated on a rotary evaporator
  5. additionafter addition of 2 drops of triethylamine
  6. concentrationconcentration the residue
  7. customis chromatographed on silica gel (dichloromethane/ethylacetate=10/3)

Sources & evidence

ORD record
ord-5812d03d115e4ba483aa1fff2eb242c5
Source dataset
uspto-grants-1988_01
Patent number
US04720491

Reaction notes

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