Acetic Acid → Ceftizoxime

HRID 1460149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1460149
[CH3:1][O:2]/[N:3]=[C:4](\[C:11]([NH:13][C@@H:14]1[C:17](=[O:18])[N:16]2[C:19]([C:23]([O-:25])=[O:24])=[CH:20][CH2:21][S:22][C@H:15]12)=[O:12])/[C:5]1[N:9]=[C:8]([NH2:10])[S:7][CH:6]=1.[Na+].C(O)(=O)C>O>[CH3:1][O:2]/[N:3]=[C:4](\[C:11]([NH:13][C@@H:14]1[C:17](=[O:18])[N:16]2[C:19]([C:23]([OH:25])=[O:24])=[CH:20][CH2:21][S:22][C@H:15]12)=[O:12])/[C:5]1[N:9]=[C:8]([NH2:10])[S:7][CH:6]=1

Komponenten

4

Edukt 2

HCID 176Acetic AcidHCID 23663938Ceftizoxime sodium

Produkt 1

HCID 6533629CeftizoximeAusbeute 91,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 5.40 mmol of ceftizoxime sodium salt (equivalent to 2 g of ceftizoxime) in 20 ml of water was acidified with 5.40 ml of 1N acetic acid. The resulting solid was collected and washed with ice water to give 1.90 g of ceftizoxime. A suspension of 1.85 g of ceftizoxime (dried at 80° C./0.1 mm) in 60 ml of methylene chloride was stirred overnight under argon with 2.03 g of N,O-bis(trimethylsilyl) acetamide and 1.73 g of diethyl chlorophosphate, whereupon the solid had dissolved. After a month the reaction mixture was evaporated to dryness and the residue was washed with water. The aqueous washes were extracted with chloroform, back-washing the chloroform extracts with water. Evaporation of the dried (MgSO4) chloroform extracts left 0.049 g of a colorless gum; NMR (CDCl3, 80 MHz) δ 1.37 (t, CH3) δ 1.41 (t, CH3), 4.17 (OCH2, NOCH3); IR (KBr) 1032 (P=O), 1787 (β-lactam).

Aufarbeitung

  1. customThe resulting solid was collected
  2. washwashed with ice water

Quellen und Nachweise

ORD-Eintrag
ord-1e03d32cf97e4f80a40b66889317ea18
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05070082

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