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

HRID 1981202Notes

Reaction equation

HRID 1981202 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].[O:23]([CH2:30][C:31]([CH:33]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>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:33][C:31](=[O:32])[CH2:30][O:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:11]([C:18]([OH:20])=[O:19])[C:10]1([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 11015099PhenoxyacetylmethylenetriphenylphosphoraneHCID 86740043Methylene-6,7-dioxo-3,3-dimethyl-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate

Product 1

HCID 86740044methylene-(2S,5R)-3,3-dimethyl-7-oxo-6-(2-oxo-3-phenoxypropylidene)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3.7 g of methylene-6,7-dioxo-3,3-dimethyl-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate in 100 ml of benzene is treated at room temperature with 4.7 g of phenoxyacetylmethylenetriphenylphosphorane. 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-7-oxo-6-(2-oxo-3-phenoxypropylidene)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate as a yellow oil [Rf: 0.44; cyclohexane/ethyl acetate (6:4); NMR (CDCl3), δ (ppm): 1.21 (9H); 1.51 (3H); 1.56 (3H); 4.58 (1H); 5.66 (2H); 5.83 (2H); 6.05 (1H); 6.8-7.45 (6H)].

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-4516d1ae6c814545b5f9d8186e886b2c
Source dataset
uspto-grants-1985_04
Patent number
US04512999

Reaction notes

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