m-Chloroperbenzoic acid → 2,2,2-Trichloroethyl 2chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate-1-oxide

HRID 2083152Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2083152
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]([Cl:40])([Cl:39])[CH2:14][O:15][C:16]([CH:18]1[N:22]2[C:23](=[O:35])[CH:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:21]2[S:20][C:19]1([CH2:37][Cl:38])[CH3:36])=[O:17]>C(Cl)(Cl)Cl>[Cl:38][CH2:37][C:19]1([CH3:36])[CH:18]([C:16]([O:15][CH2:14][C:13]([Cl:39])([Cl:12])[Cl:40])=[O:17])[N:22]2[C:23](=[O:35])[CH:24]([NH:25][C:26](=[O:34])[CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:21]2[S:20]1=[O:9]

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 128952672,2,2-Trichloroethyl 2-chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate

Produkt 1

HCID 705905452,2,2-Trichloroethyl 2chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate-1-oxideAusbeute 79,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

A solution of m-chloroperbenzoic acid (2.03 g) in chloroform (30 ml) was added dropwise to a solution of 2,2,2-trichloroethyl-2-chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate (5.0 g) in chloroform (40 ml) at -10° - -5° C under stirring, and then the mixture was stirred at -10° - -5° C for 1 hour. After the solid was filtered off, the filtrate was washed with a saturated sodium bicarbonate aqueous solution and water, in turn, and then dried over magnesium sulfate. After removal of solvent, the residue was crystallized by adding ethanol. The crystal was filtered and recrystallized from ethanol to give 2,2,2-trichloroethyl 2-chloromethyl-2-methyl-6-(2-phenylacetamido)penam-3-carboxylate-1-oxide (4.10 g), mp 130° - 131° C.

Aufarbeitung

  1. stirringthe mixture was stirred at -10° - -5° C for 1 hour
  2. filtrationAfter the solid was filtered off
  3. washthe filtrate was washed with a saturated sodium bicarbonate aqueous solution and water, in turn
  4. dry with materialdried over magnesium sulfate
  5. customAfter removal of solvent
  6. customthe residue was crystallized
  7. additionby adding ethanol
  8. filtrationThe crystal was filtered
  9. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-dea750fc1c534085af24344c8431046f
Quelldatensatz
uspto-grants-1978_04
Patentnummer
US04084049

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