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

HRID 1981209Notes

Reaction equation

HRID 1981209 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].C1(P(C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:30][C:31]([CH2:33][Cl:34])=[O:32])C=CC=CC=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:30][C:31]([CH2:33][Cl:34])=[O:32])[C@@H:11]([C:18]([OH:20])=[O:19])[C:10]1([CH3:22])[CH3:21]

Participants

4

Reactant 2

HCID 86740043Methylene-6,7-dioxo-3,3-dimethyl-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalateHCID 178520789HCID 178520789, compound

Product 1

HCID 86740057methylene-(2S,5R)-6-(3-chloroacetonylidene)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 6.6 g of methylene-6,7-dioxo-3,3-dimethyl-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate in 150 ml of benzene is treated at room temperature with 9 g of triphenylchloroacetonylphosphorane. After 10 minutes, the reaction mixture is evaporated. The residue is chromatographed on silica gel while eluting with cyclohexane/ethyl acetate (7:3). There is obtained methylene-(2S,5R)-6-(3-chloroacetonylidene)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate as an orange oil [Rf: 0.4; cyclohexane/ethyl acetate (6:4); NMR (CDCl3), δ (ppm); 1.21 (9H); 1.51 (3H); 1.57 (3H); 4.25 (2H); 4.65 (1H); 5.9 (m, 2H); 6.1 (1H); 6.93 (1H)].

Workup

  1. customthe reaction mixture is evaporated
  2. customThe residue is chromatographed on silica gel
  3. washwhile eluting with cyclohexane/ethyl acetate (7:3)

Sources & evidence

ORD record
ord-226af6d9786f44e7971fff10e56e5ca2
Source dataset
uspto-grants-1985_04
Patent number
US04512999

Reaction notes

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