Methyl Isobutyl Ketone → Sodium (Z)-(2S,3S,5R)-3-(2-cyanoethenyl)-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

HRID 263744

Reaction equation

[C:1](/[CH:3]=[CH:4]\[C@:5]1([CH3:31])[S:11](=[O:13])(=[O:12])[C@H:10]2[N:7]([C:8](=[O:14])[CH2:9]2)[C@H:6]1[C:15]([O:17]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:16])#[N:2].CC(CC(C)C)=O.C(C(CCCC)C([O-])=O)C.[Na+:49]>C1C(O)=CC=CC=1C>[C:1](/[CH:3]=[CH:4]\[C@:5]1([CH3:31])[S:11](=[O:13])(=[O:12])[C@H:10]2[N:7]([C:8](=[O:14])[CH2:9]2)[C@H:6]1[C:15]([O-:17])=[O:16])#[N:2].[Na+:49]

Participants

Conditions

Temperature: 50 °C

Procedure

95 mg (0.2 mmol) of benzhydryl (Z)-(2S,3S,5R)-3-(2-cyanoethenyl)- 3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate were dissolved in 3 ml of m-cresol and stirred at 50° C. for 45 minutes. The reaction mixture was treated with 10 ml of isobutyl methyl ketone and 120 μl of sodium 2-ethylcaproate (2N in ethyl acetate, 1.1 eq.). The mixture was extracted twice with 3 ml of water each time, the combined aqueous phases are washed with 10 ml of isobutyl methyl ketone and lyophilized. The yellow lyophilizate was dissolved in 1.3 ml of water and chromatographed over polymeric hydrophobic gel. Yield: 50 mg (80%) of colorless lyophilizate IR (KBr): 2222, 1782, 1626, 1395, 1323, 1141 cm-1 1 H-NMR (250MHz, D2O): δ[ppm]=1.94(s,3H), 3.47(dd,1H,J=16Hz, 1.6Hz, 6-H), 3.73(dd, 1H, J=16Hz, 4.4Hz, 6-H), 4.80(s,1H,2-H), 5.19(dd, 1H, J=16Hz, 4.4Hz,5-H), 6.15(d.1H,J=12Hz,=CH), 6.68 (d,1 H,J=12Hz,=CH).

Workup

extractionThe mixture was extracted twice with 3 ml of water each time
washthe combined aqueous phases are washed with 10 ml of isobutyl methyl ketone
dissolutionThe yellow lyophilizate was dissolved in 1.3 ml of water
customchromatographed over polymeric hydrophobic gel

Sources & evidence

ORD record: ord-56a208715fcd48fbb7c72d5f3d89da62
Source dataset: uspto-grants-1997_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05644053

Linked notes

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