m-Chloroperbenzoic acid → 2,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate-1-oxide

HRID 851583Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851583
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[S:14][C@@H:15]2[CH:28]([NH:29][C:30](=[O:38])[CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:27](=[O:39])[N:16]2[CH:17]([C:19]([O:21][CH2:22][C:23]([Cl:26])([Cl:25])[Cl:24])=[O:20])[CH:18]=1>ClCCl>[CH3:12][CH:13]1[CH:18]=[C:17]([C:19]([O:21][CH2:22][C:23]([Cl:24])([Cl:25])[Cl:26])=[O:20])[N:16]2[C:27](=[O:39])[CH:28]([NH:29][C:30](=[O:38])[CH2:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C@H:15]2[S:14]1=[O:9]

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 131803442,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-2-cephem-4-carboxylate

Produkt 1

HCID 705266812,2,2-Trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate-1-oxideAusbeute 58,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A solution of 3-chloroperbenzoic acid (0.40 g.) in dichloromethane (10 ml.) was dropwise added to a solution of 2,2,2-trichloroethyl 2-methyl-7-(2-phenylacetamido)-2-cephem-4-carboxylate (0.92 g.) in dichloromethane (10 ml.) and the mixture was stirred for 1 hour. After the reaction was completed, the reaction mixture was filtered and the filtrate was washed in turn with a sodium bicarbonate aqueous solution and a saturated sodium chloride aqueous solution, dried over magnesium sulfate, after which the solvent was distilled off under reduced pressure. The residue was recrystallized from ethanol to give 2,2,2-trichloroethyl 2-methyl-7-(2-phenylacetamido)-3-cephem-4-carboxylate-1-oxide (0.56 g.), mp 173° to 175° C.

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. washthe filtrate was washed in turn with a sodium bicarbonate aqueous solution
  3. dry with materiala saturated sodium chloride aqueous solution, dried over magnesium sulfate
  4. distillationafter which the solvent was distilled off under reduced pressure
  5. customThe residue was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-5632cce1604a4fe18138cf7116c26994
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04385176

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