Reaktion #350930

ord-2d31df2eeb1243bfb4703d994334a0b8

Reaktionsgleichung

C[C@]1(/C=C/c2ncon2)[C@H](C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C[C@H]2S1(=O)=O
benzhydryl (E)-(2S,3S,5R)-3-methyl-3-[2-(1,2,4-oxadiazol-3-yl)-vinyl]-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate
CCCCCC
n-hexane
→
C[C@]1(/C=C/c2ncon2)[C@H](C(=O)O)N2C(=O)C[C@H]2S1(=O)=O
(E)-(2S,3S,5R)-3-methyl-3-[2-(1,2,4-oxadiazol-3-yl)- vinyl]-4,4,7-trioxo-4-thia-1-aza-bicyclo [3.2.0]heptane-2-carboxylic acid

Edukte

C[C@]1(/C=C/c2ncon2)[C@H](C(=O)OC(c2ccccc2)c2ccccc2)N2C(=O)C[C@H]2S1(=O)=O
benzhydryl (E)-(2S,3S,5R)-3-methyl-3-[2-(1,2,4-oxadiazol-3-yl)-vinyl]-4,4,7-trioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate
CCCCCC
n-hexane

Reagenzien

Keine

Lösungsmittel

Cc1cccc(O)c1
m-cresol

Reaktionsbedingungen

Temperatur
50°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationthe separated crystals were filtered off under suction
  2. 2
    Waschenrinsed with n-hexane
  3. 3
    SonstigeThe crude crystallizate was recrystallized from ethyl acetate/n-hexane

Vorschrift

355 mg (0.74 mmol) of benzhydryl (E)-(2S,3S,5R)-3-methyl-3-[2-(1,2,4-oxadiazol-3-yl)-vinyl]-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 4 hours. 20 ml of n-hexane are added to the pale brown solution, the separated crystals were filtered off under suction and rinsed with n-hexane. The crude crystallizate was recrystallized from ethyl acetate/n-hexane. Yield: 170 mg (73%) of colorless crystals MS: (M--H)- 312.2 IR (KBr): 2900(br), 1811, 1714, 1660, 1331, 1194, 980 cm-1M.p.: 161° C. (dec.) Elementary analysis: C11H11N3O6S (313.284) Calc. C 42.17 H 3.54 N 13.41 Found C 42.41 H 3.64 N 13.18

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05644053uspto-grants-1997_07