Diethyl [2-oxo-3-(triphenylphosphoranylidene)propyl]phosphonate → methylene-(2S,5R)-6-[(Z)-acetonylidene]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate

HRID 1981208Notes

Reaction equation

HRID 1981208 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].[CH2:23]([O:25][P:26]([CH2:31][C:32]([CH:34]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:33])([O:28][CH2:29][CH3:30])=[O:27])[CH3:24]>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:34][C:32](=[O:33])[CH2:31][P:26]([O:28][CH2:29][CH3:30])([O:25][CH2:23][CH3:24])=[O:27])[C@@H:11]([C:18]([OH:20])=[O:19])[C:10]1([CH3:22])[CH3:21].[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:31]/[C:32]([CH3:34])=[O:33])[C@@H:11]([C:18]([OH:20])=[O:19])[C:10]1([CH3:22])[CH3:21]

Participants

5

Reactant 2

HCID 4361785Diethyl [2-oxo-3-(triphenylphosphoranylidene)propyl]phosphonateHCID 86740043Methylene-6,7-dioxo-3,3-dimethyl-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate

Product 2

HCID 86740041methylene-(2S,5R)-6-[(Z)-acetonylidene]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalateHCID 86740056methylene-(2S,5R)-6-[3-(diethoxyphosphinyl)-2-oxopropylidene]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate pivalate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1.0 g of methylene-6,7-dioxo-3,3-dimethyl-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate pivalate in 30 ml of benzene is treated at room temperature with 1.8 g of diethoxyphosphinylacetylmethylenetriphenylphosphorane. After 10 minutes, the reaction mixture is evaporated. The residue is chromatographed on silica gel while eluting with ethyl acetate. There is obtained methylene-(2S,5R)-6-[3-(diethoxyphosphinyl)-2-oxopropylidene]-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate pivalate as a yellow oil [Rf: 0.35; ethyl acetate; NMR (CDCl3), δ (ppm): 1.23 (9H); 1.36 (3H); 1.51 (3H); 1.59 (3H); 3.12 and 3.42 (2H, P-CH2); 4.21 (4H); 4.63 (1H); 5.90 (2H): 6.08 (1H); 6.82 (1H)].

Workup

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

Sources & evidence

ORD record
ord-f958f0b062c14350a4b5c6e4a476ee0c
Source dataset
uspto-grants-1985_04
Patent number
US04512999

Reaction notes

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