benzhydryl (E)-(2S,3S,5R)-3-(2-chloro-vinyl)-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate → Sodium (E)-(2S,3S,5R)-3-(2-chloro-vinyl)-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

HRID 1683169Notes

Reaction equation

[Cl:1]/[CH:2]=[CH:3]/[C@:4]1([CH3:30])[S:10](=[O:12])(=[O:11])[C@H:9]2[N:6]([C:7](=[O:13])[CH2:8]2)[C@H:5]1[C:14]([O:16]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:15].C(C(CCCC)C([O-])=O)C.[Na+:41]>C1C(O)=CC=CC=1C.CC(CC(C)C)=O>[Cl:1]/[CH:2]=[CH:3]/[C@:4]1([CH3:30])[S:10](=[O:12])(=[O:11])[C@H:9]2[N:6]([C:7](=[O:13])[CH2:8]2)[C@H:5]1[C:14]([O-:16])=[O:15].[Na+:41]

Participants

Conditions

Temperature: 50 °C

Procedure

385 mg (0.86 mmol) of benzhydryl (E)-(2S,3S,5R)-3-(2-chloro-vinyl)-3-methyl-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate are dissolved in 2.3 ml of m-cresol under argon and stirred at 50° C. for 4 hours. Subsequently, the mixture was diluted with 15 ml of isobutyl methyl ketone, treated with 0.50 ml of sodium 2-ethylcaproate (2N solution in ethyl acetate) and extracted three times with 8 ml of water each time. The combined aqueous phases were washed once with 10 ml of isobutyl methyl ketone, lyophilized and the lyophilizate obtained was chromatographed over polymeric hydrophobic gel with water as the eluent.

Workup

extractionextracted three times with 8 ml of water each time
washThe combined aqueous phases were washed once with 10 ml of isobutyl methyl ketone
customthe lyophilizate obtained
customwas chromatographed over polymeric hydrophobic gel with water as the eluent

Sources & evidence

ORD record: ord-caef1bfdd59e4d948dcf205bd3a317fa
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05637579

Reaction notes

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