m-Chloroperbenzoic acid → Methyl acetate hexane

HRID 127647

Reaktionsgleichung

Reaktionsgleichung von HRID 127647
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](C(OO)=O)[CH:3]=1.C1([CH:18]([O:25][C:26]([C:28]2N3C(=O)[C@@H](NC(=O)COC4C=CC=CC=4)[C@H]3SCC=2SC2N(C)N=NN=2)=[O:27])C2C=CC=CC=2)C=CC=CC=1.C1(C(OC(C2N3C(=O)[C@@H](NC(=O)COC4C=CC=CC=4)[C@H]3SC=C2SC2N(C)N=NN=2)=O)C2C=CC=CC=2)C=CC=CC=1>C(Cl)(Cl)Cl>[C:26]([O:25][CH3:18])(=[O:27])[CH3:28].[CH3:6][CH2:7][CH2:2][CH2:3][CH2:4][CH3:5]

Komponenten

5

Edukt 3

HCID 70297m-Chloroperbenzoic acidHCID 705628767beta-Phenoxyacetylamino-3-(1-methyl-5-tetrazolylthio)-2-cephem-4-carboxylic acid diphenylmethyl esterHCID 705631007beta-Phenoxyacetylamino-3-(1-methyl-5-tetrazolylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester2×

Produkt 1

HCID 23449302Methyl acetate hexane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

10.35 g (51.1 mmols) of m-chloroperbenzoic acid (85% strength) are added to a solution of 20.7 g (33.8 mmols) of a mixture consisting of 7β-phenoxyacetylamino-3-(1-methyl-5-tetrazolylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester and 7β-phenoxyacetylamino-3-(1-methyl-5-tetrazolylthio)-2-cephem-4-carboxylic acid diphenylmethyl ester in 350 ml of chloroform at 0° C. and the mixture is stirred for 2 hours. Excess per acid is then destroyed by adding 85 ml of 0.1 N sodium thiosulphate. The reaction solution is extracted with aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution and the organic phase is dried over sodium sulphate and concentrated in vacuo. The residue is dried in a high vacuum and gives a mixture of the 1β-oxide and 1α-oxide of 7β-phenoxyacetylamino-3-(1-methyl-5-tetrazolylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester; thin layer chromatogram: silica gel (toluene/ethyl acetate, 1:2), β-sulphoxide: Rf=0.26; α -sulphoxide: Rf=0.13. The two sulphoxides are chromatographed on 1 kg of silica gel with toluene/ethyl acetate, 1:2, and the pure β-sulphoxide of melting point 146° C. (from methyl acetate/hexane; IR spectrum (nujol): characteristic bands at 3.05; 5.58; 5.78; 5.83 and 5.97μ), and the pure α-sulphoxide of melting point 180° C. (decomposition; from methylene chloride/diethyl ether; IR spectrum (nujol): characteristic bands at 2.95; 5.53; 5.77 and 5.92μ) are obtained.

Aufarbeitung

  1. customExcess per acid is then destroyed
  2. additionby adding 85 ml of 0.1 N sodium thiosulphate
  3. extractionThe reaction solution is extracted with aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue is dried in a high vacuum
  7. customgives
  8. customThe two sulphoxides are chromatographed on 1 kg of silica gel with toluene/ethyl acetate, 1:2

Quellen und Nachweise

ORD-Eintrag
ord-85d2f8cb5dee47c1967db9bf9bb4fa9b
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04256739

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