Ammonia → Cephalexin

HRID 126681

Reaktionsgleichung

Reaktionsgleichung von HRID 126681
[CH3:1][C:2]1[CH2:11][S:10][C@@H:5]2[C@H](N)[C:7](=[O:8])[N:4]2[C:3]=1[C:12]([OH:14])=[O:13].C[Si](C)(C)N[Si](C)(C)C.[CH3:24][N:25]1[CH2:29][CH2:28][CH2:27][C:26]1=[O:30].[NH3:31]>C(#N)C.O>[CH3:1][C:2]1[CH2:11][S:10][C@@H:5]2[C@H:24]([NH:25][C:26]([C@H:27]([NH2:31])[C:28]3[CH:1]=[CH:2][CH:3]=[CH:12][CH:29]=3)=[O:30])[C:7](=[O:8])[N:4]2[C:3]=1[C:12]([OH:14])=[O:13]

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 13387N-methyl-2-pyrrolidoneHCID 13838HexamethyldisilazaneHCID 334987-Aminodeacetoxycephalosporanic acid

Produkt 1

HCID 27447Cephalexin

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

21.4 g of 7-aminodesacetoxycephalosporanic acid were suspended in 450 ml of acetonitrile, and then 17.7 g of hexamethyldisilazane were added to the suspension. The mixture was heated to 65° C. for 2 hours under a nitrogen atmosphere and then cooled to 15° C. 22 g of N-methylpyrrolidone were added. After 10 minutes, 22.5 g of D(-)-phenylglycyl chloride hydrochloride were added and the mixture was stirred at 15° C. for 4 hours and then added to 500 ml of water at 10° C. Aqueous ammonia was then added to the reaction mixture to precipitate the desired product which, after 10 hours, was filtered off and dried. 25 g of cephalexin [7-(D-α-aminophenylacetamido)desacetoxycephalosporanic acid] were obtained. Iodometric assay against an authentic sample showed that the product was 98.7% pure.

Aufarbeitung

  1. temperaturecooled to 15° C
  2. customto precipitate the desired product which
  3. waitafter 10 hours
  4. filtrationwas filtered off
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8462c04765964b208263dbc475472026
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04254029

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