Hydrochloric Acid → 7-D-mandelamido-3-(((1-sulfomethyl-1H-tetrazol-5-yl)thio)methyl)-3-cephem-4-carboxylic acid

HRID 18690

Reaktionsgleichung

Reaktionsgleichung von HRID 18690
[NH2:1][CH:2]1[C:24](=[O:25])[N:4]2[C:5]([C:21]([OH:23])=[O:22])=[C:6]([CH2:9][S:10][C:11]3[N:15]([CH2:16][S:17]([OH:20])(=[O:19])=[O:18])[N:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12.[OH-].[Na+].[C:28](=[O:31])(O)[O-].[Na+].Cl.[C:34]([OH:37])(=O)[CH3:35].[C:38](O)(=O)[CH3:39].[CH2:42]([NH:46][CH2:47][CH2:48][NH:49][CH2:50][CH:51]([CH3:53])[CH3:52])[CH:43]([CH3:45])[CH3:44]>O.C(O)(C)C>[CH2:50]([NH:49][CH2:48][CH2:47][NH:46][CH2:42][CH:43]([CH3:45])[CH3:44])[CH:51]([CH3:52])[CH3:53].[C:28]([NH:1][CH:2]1[C:24](=[O:25])[N:4]2[C:5]([C:21]([OH:23])=[O:22])=[C:6]([CH2:9][S:10][C:11]3[N:15]([CH2:16][S:17]([OH:20])(=[O:18])=[O:19])[N:14]=[N:13][N:12]=3)[CH2:7][S:8][C@H:3]12)(=[O:31])[C@@H:34]([C:35]1[CH:39]=[CH:38][CH:44]=[CH:43][CH:42]=1)[OH:37]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium Bicarbonate2×HCID 85588787N,N'-diisobutylethylenediamine diacetateHCID 875069217-Amino-3-(sulfomethyl-1h-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

Produkt 2

HCID 4699001,2-Ethanediamine, N,N'-bis(2-methylpropyl)-HCID 450061447-D-mandelamido-3-(((1-sulfomethyl-1H-tetrazol-5-yl)thio)methyl)-3-cephem-4-carboxylic acidAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
7.5 °C

Versuchsvorschrift

7-amino-3-(1-sulfomethyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (5 g) was dissolved in water (19 ml) using 30% w/w sodium hydroxide (1.5 g in 8 ml water) and sodium bicarbonate (1 g), O-formylmandeloyl chloride (2.45 g) was added at 0-5° C. and maintained at 5-10° C. over a period of 1-2 hours. After the completion of reaction, the reaction mixture was acidified with conc. HCl (2.6 g) and maintained the reaction at 28-30° C. for about 2-3 hrs, sodium bicarbonate (3.5 g) was added to set the pH 5±1 and the reaction mass solution was added to a solution of N,N′-diisobutylethylenediamine diacetate (8.2 g) in water (40 mL) and isopropyl alcohol (40 mL) and stirred well at 25-30° C. for about 2-3 hours. The reaction mixture was cooled to 5-10° C., filtered, washed with chilled water (0-5° C.) followed by isopropyl alcohol (0-5° C.) and dried the material at ˜40° C. to get N,N′-diisobutylethylenediamine salt of 7-D-mandelamido-3-(((1-sulfomethyl-1H-tetrazol-5-yl)thio)methyl)-3-cephem-4-carboxylic acid (5.5 g). Step(ii)

Aufarbeitung

  1. additionwas added at 0-5° C.
  2. customAfter the completion of reaction
  3. temperaturemaintained
  4. customthe reaction at 28-30° C. for about 2-3 hrs
  5. temperatureThe reaction mixture was cooled to 5-10° C.
  6. filtrationfiltered
  7. washwashed with chilled water (0-5° C.)
  8. customfollowed by isopropyl alcohol (0-5° C.)
  9. customdried the material at ˜40° C.

Quellen und Nachweise

ORD-Eintrag
ord-990d0f90a5184a249a9729eed3fd48c2
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741478B2

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