Methylene-6,7-dioxo-3,3-dimethyl-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate → HCID 86740058, compound

HRID 1981210Notes

Reaction equation

HRID 1981210 reaction equation
[C:1]([OH:7])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].C=[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].C(OC(C1C=CC=CC=1P(=CC(=O)C=NOC)(C1C=CC=CC=1)C1C=CC=CC=1)=O)C>C1C=CC=CC=1>[C:1]([OH:7])(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:21][C:10]1([CH3:22])[S:9][CH:15]2[N:12]([C:13](=[O:17])[CH2:14]2)[CH:11]1[C:18]([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 86740043Methylene-6,7-dioxo-3,3-dimethyl-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalateHCID 86740059HCID 86740059, compound

Product 1

HCID 86740058HCID 86740058, compound

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 11 g of ethoxycarbonyl(methoxyimino)acetylmethylenetriphenylphosphorane. 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)-6-[3-ethoxycarbonyl)-2-(Z)-(methoxyimino)acetonylidene]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate pivalate as an orange oil [Rf: 0.51; cyclohexane/ethyl acetate (6:4); NMR (CDCl3), δ (ppm): 1.23 (9H); 1.37 (m, 3H); 1.53 (3H); 1.62 (3H); 4.21 (3H, --OCH3); 4.42 (m, 2H); 4.65 (1H3); 5.9 (m, 2H); 6.11 (1H); 6.66 (1H)].

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-a5663b93609c43058065c787ea5fbef4
Source dataset
uspto-grants-1985_04
Patent number
US04512999

Reaction notes

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