Methylsulphonylacetylmethylenetriphenylphosphorane → methylene-(2S,5R)-3,3-dimethyl-7-oxo-6-[3-methylsulphonyl-2-oxopropylidene]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate

HRID 1981211Notes

Reaction equation

HRID 1981211 reaction equation
[C:1]([OH:7])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH2:8]=[S:9]1[CH:15]2[N:12]([C:13](=[O:17])[C:14]2=O)[CH:11]([C:18]([OH:20])=[O:19])[C:10]1([CH3:22])[CH3:21].[CH3:23][S:24]([CH2:27][C:28]([CH:30]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:29])(=[O:26])=[O:25]>C1C=CC=CC=1>[C:1]([OH:7])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH2:8]=[S:9]1[C@H:15]2[N:12]([C:13](=[O:17])[C:14]2=[CH:30][C:28](=[O:29])[CH2:27][S:24]([CH3:23])(=[O:26])=[O:25])[C@@H:11]([C:18]([OH:20])=[O:19])[C:10]1([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 20400056MethylsulphonylacetylmethylenetriphenylphosphoraneHCID 86740043Methylene-6,7-dioxo-3,3-dimethyl-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate

Product 1

HCID 86740060methylene-(2S,5R)-3,3-dimethyl-7-oxo-6-[3-methylsulphonyl-2-oxopropylidene]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2.3 g of methylene-6,7-dioxo-3,3-dimethyl-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate in 75 ml of benzene is treated at room temperature with 4 g of methylsulphonylacetylmethylenetriphenylphosphorane. After 10 minutes, the reaction mixture is evaporated. The residue is chromatographed on silica gel while eluting with cyclohexane/ethyl acetate (1:1). There is obtained methylene-(2S,5R)-3,3-dimethyl-7-oxo-6-[3-methylsulphonyl-2-oxopropylidene]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate as an orange oil [Rf: 0.23; cyclohexane/ethyl acetate (1:1); NMR (CDCl3), δ (ppm): 1.22 (9H); 1.5 (3H); 1.56 (3H); 3.03 (3H, CH3 --SO2); 4.24 (2H, --CH2 --SO2); 4.59 (1H); 6.02 (1H); 6.79 (1H)].

Workup

  1. customthe reaction mixture is evaporated
  2. customThe residue is chromatographed on silica gel
  3. washwhile eluting with cyclohexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-6f0d4fc423d3436fbdc35cd6cdd2e494
Source dataset
uspto-grants-1985_04
Patent number
US04512999

Reaction notes

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