7-Aminocephalosporanic acid → 7-Amino-3-(4,6-diamino-pyrimidin-2-yl-thiomethyl)-ceph-3-em-4-carboxylic acid dihydrate

HRID 1277810Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1277810
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=[O:3].[NH2:19][C:20]1[CH:25]=[C:24]([NH2:26])[N:23]=[C:22]([SH:27])[N:21]=1>O.C(=O)(O)[O-].[Na+]>[OH2:3].[OH2:3].[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:27][C:22]3[N:23]=[C:24]([NH2:26])[CH:25]=[C:20]([NH2:19])[N:21]=3)[CH2:15][S:14][C@H:9]12

Komponenten

5

Edukt 2

HCID 4413287-Aminocephalosporanic acidHCID 1785079174,6-diaminopyrimidine-2-thiol

Produkt 1

HCID 676616387-Amino-3-(4,6-diamino-pyrimidin-2-yl-thiomethyl)-ceph-3-em-4-carboxylic acid dihydrateAusbeute 82,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2.7 g (0.01 mole) of 7-aminocephalosporanic acid are dissolved in 50 ml of water with the required amount of sodium bicarbonate. 1.7 g (0.013 mole) of 4,6-diamino-2-mercaptopyrimidine and the equivalent amount of sodium bicarbonate are added and the reaction solution is heated to 60° C. for 4 hours, whilst stirring and keeping the pH value constant (pH=7). The mixture is allowed to cool, undissolved material is filtered off and the filtrate is concentrated in vacuo at 30° C. to half its volume. The aqueous solution which remains is extracted several times with ethyl acetate and the aqueous phase is adjusted to a pH of 2 with 2 N hydrochloric acid. The precipitate is filtered off, washed with water until free from chloride and dried in vacuo at 37° C. over potassium hydroxide. 1.61 g of the title compound are obtained. Rf : 0.27 (acetone:glacial acetic acid =10:1) IR (KBr): 1,745 cm-1 (β-lactam band) NMR (d6 -DMSO, 60 MHz):

Aufarbeitung

  1. temperatureto cool
  2. filtrationundissolved material is filtered off
  3. concentrationthe filtrate is concentrated in vacuo at 30° C. to half its volume
  4. extractionThe aqueous solution which remains is extracted several times with ethyl acetate
  5. filtrationThe precipitate is filtered off
  6. washwashed with water until free from chloride
  7. dry with materialdried in vacuo at 37° C. over potassium hydroxide

Quellen und Nachweise

ORD-Eintrag
ord-1f716ead5e51485198b38dcbe2085798
Quelldatensatz
uspto-grants-1981_07
Patentnummer
US04278793

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