Pyridine → 7-Phenoxyacetamido-3-methyl-3-cephem-4-carboxylic acid

HRID 1730706

Reaktionsgleichung

Reaktionsgleichung von HRID 1730706
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:24](=[O:25])[N:14]2[CH:15]([C:21]([OH:23])=[O:22])[C:16]([CH3:20])([CH2:18]Br)[S:17][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.C[Si](Cl)(C)C.C(OCC)(=O)C>C1C=CC=CC=1>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:24](=[O:25])[N:14]2[C:15]([C:21]([OH:23])=[O:22])=[C:16]([CH3:20])[CH2:18][S:17][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 1049Pyridine2×HCID 6397ChlorotrimethylsilaneHCID 8857Ethyl AcetateHCID 128952582-Bromomethyl-2-methyl-6-(2-phenoxyacetamido)penam-3-carboxylic acid

Produkt 1

HCID 155734007-Phenoxyacetamido-3-methyl-3-cephem-4-carboxylic acidAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

6-(2-phenoxyacetamido)-2-methyl-2-bromomethylpenam-3-carboxylic acid (429 mg.) was suspended in dry benzene (10 cc), and pyridine (400 mg.) and trimethylsilylchloride (5 cc) were added thereto. The mixture was stirred for 1.5 hours at room temperature and pyridine (400 mg.) was added thereto. The mixture was heated under reflux for 3 hours, mixed with ethyl acetate (30 cc), washed with dilute phosphoric acid and further with an aqueous solution saturated with sodium chloride, dried and then concentrated. A small amount of ethyl acetate was added to the residue and the precipitate was collected by filtration to yield crystals (250 mg.) of 7-(2-phenoxyacetamido)-3-methyl-3-cephem-4-carboxylic acid, m.p. 170.5° - 172° C.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. washwashed with dilute phosphoric acid and further with an aqueous solution saturated with sodium chloride
  4. customdried
  5. concentrationconcentrated
  6. additionA small amount of ethyl acetate was added to the residue
  7. filtrationthe precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-62db17ec99264e02a0c05500f94c7238
Quelldatensatz
uspto-grants-1976_11
Patentnummer
US03993646

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