m-Chloroperbenzoic acid → p-Nitrobenzyl(1RS,5S,6S)-2-phenylsulfinyl-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

HRID 622442Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 622442
C(=O)(O)[O-:2].[Na+].ClC1C=CC=C(C(OO)=O)C=1.[C:17]1([S:23][C:24]2[CH:25]([CH3:48])[C@@H:26]3[C@@H:43]([C@H:44]([OH:46])[CH3:45])[C:42](=[O:47])[N:27]3[C:28]=2[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[C:17]1([S:23]([C:24]2[CH:25]([CH3:48])[C@@H:26]3[C@@H:43]([C@H:44]([OH:46])[CH3:45])[C:42](=[O:47])[N:27]3[C:28]=2[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)=[O:30])=[O:2])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 22839821p-Nitrobenzyl (1RS,5S,6S)-2-phenylthio-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Produkt 1

HCID 22839820p-Nitrobenzyl(1RS,5S,6S)-2-phenylsulfinyl-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

19 ml of saturated aqueous sodium bicarbonate solution and a solution of 350 mg of 3-chloroperbenzoic acid in 10 ml of methylene chloride were added to a solution of 360 mg of p-nitrobenzyl(1RS,5S,6S)-2-phenylthio-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate in 19 ml of methylene chloride, kept at 0° to 5° C. with ice-water cooling, and the mixture was stirred for 35 minutes at the same temperature. The reaction mixture was then diluted with methylene chloride and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was purified by chromatography on a column of silica gel, using a 1/8 mixture of benzene and ethyl acetate as eluent, giving 200 mg of the title compound.

Aufarbeitung

  1. washwashed with saturated aqueous sodium chloride solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customThe residue was purified by chromatography on a column of silica gel
  5. additiona 1/8 mixture of benzene and ethyl acetate as eluent

Quellen und Nachweise

ORD-Eintrag
ord-b303b213974a42bab756c8ca0a7866df
Quelldatensatz
uspto-grants-1988_09
Patentnummer
US04771046

Notizen zur Reaktion

Wird geladen…