Hydrochloric Acid → 7alpha-Chloro-3-methyl-3-cephem-4-carboxylic acid

HRID 257801

Reaktionsgleichung

Reaktionsgleichung von HRID 257801
[CH3:1][C:2]1[CH2:11][S:10][C@@H:5]2[C@H:6](N)[C:7](=[O:8])[N:4]2[C:3]=1[C:12]([OH:14])=[O:13].C(O)C.[ClH:18].N([O-])=O.[Na+]>[Cl-].[Na+].O.O>[Cl:18][C@H:6]1[C:7](=[O:8])[N:4]2[C:3]([C:12]([OH:14])=[O:13])=[C:2]([CH3:1])[CH2:11][S:10][C@H:5]12

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 334987-Aminodeacetoxycephalosporanic acidHCID 23668193Sodium Nitrite

Produkt 1

HCID 156604937alpha-Chloro-3-methyl-3-cephem-4-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

A mixture of 7-ADCA (25 g, 0.117 mol), ethanol (700 ml), water (163 ml) and concentrated hydrochloric acid (163 ml) was cooled to 5° C. Sodium nitrite (11.5 g, 0.167 mol) was added in small portions over 25 minutes and the mixture was stirred for 3.5 hours at 0°-5° C.; 300 ml of brine was added and the reaction mixture was extracted with methylene chloride. The organic extract was washed with water, brine, dried over sodium sulfate and concentrated (16.1 g, 58.9%). This crude acid was directly used for the next step without further purification.

Aufarbeitung

  1. extractionthe reaction mixture was extracted with methylene chloride
  2. extractionThe organic extract
  3. washwas washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated (16.1 g, 58.9%)
  6. customThis crude acid was directly used for the next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-4f66a560b4d744959a2551b9024d02ec
Quelldatensatz
uspto-grants-1993_11
Patentnummer
US05264430

Verknüpfte Notizen

Wird geladen…