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

HRID 1981204Notes

Reaction equation

HRID 1981204 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].[CH:23]1[CH:28]=CC=[CH:25][CH:24]=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=[C:23]([CH3:28])[C:24](=[O:6])[CH3:25])[C@@H:11]([C:18]([OH:20])=[O:19])[C:10]1([CH3:22])[CH3:21]

Participants

3

Reactant 2

HCID 241BenzeneHCID 86740043Methylene-6,7-dioxo-3,3-dimethyl-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate

Product 1

HCID 86740049methylene-(2S,5R)-3,3-dimethyl-6-(1-methyl-2-oxopropylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate

Procedure

A solution of 7.8 g of methylene-6,7-dioxo-3,3-dimethyl-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate in 200 ml of benzene is treated at room temperature with 10 g of triphenylphosphinemethylacetylmethylene. After 10 minutes, the reaction mixture is evaporated. The residue is chromatographed on silica gel while eluting with cyclohexane/ethyl acetate (6:4). There is obtained methylene-(2S,5R)-3,3-dimethyl-6-(1-methyl-2-oxopropylidene)-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate as white crystals of melting point 59°-60° [Rf: 0.30; cyclohexane/ethyl acetate (6:4)].

Workup

  1. customthe reaction mixture is evaporated
  2. customThe residue is chromatographed on silica gel
  3. washwhile eluting with cyclohexane/ethyl acetate (6:4)

Sources & evidence

ORD record
ord-37a1e0b254404739a07b9aff8b106490
Source dataset
uspto-grants-1985_04
Patent number
US04512999

Reaction notes

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