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

HRID 18692

Reaktionsgleichung

Reaktionsgleichung von HRID 18692
[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(O)(=O)C.[CH2:42]([NH:51][CH2:52][CH2:53][NH:54][CH2:55][C:56]1[CH:61]=[CH:60][C:59]([O:62][CH3:63])=[CH:58][CH:57]=1)[C:43]1[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[CH:45][CH:44]=1>O.C(O)(C)C>[CH2:55]([NH:54][CH2:53][CH2:52][NH:51][CH2:42][C:43]1[CH:44]=[CH:45][C:46]([O:49][CH3:50])=[CH:47][CH:48]=1)[C:56]1[CH:61]=[CH:60][C:59]([O:62][CH3:63])=[CH:58][CH:57]=1.[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:47]=[CH:48][CH:43]=[CH:44][CH:45]=1)[OH:37]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium Bicarbonate2×HCID 86625397N,N'-di-(p-anisyl)ethylenediamine diacetateHCID 875069217-Amino-3-(sulfomethyl-1h-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

Produkt 2

HCID 408327N,N'-di-(p-anisyl)ethylenediamineHCID 450061447-D-mandelamido-3-(((1-sulfomethyl-1H-tetrazol-5-yl)thio)methyl)-3-cephem-4-carboxylic acidAusbeute 99,1 %

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 under stirring at 28-30° C. over 2-3 hours. After the completion of reaction, sodium bicarbonate (˜3.5 g) was added to set the pH 5±1. The solution was added to a solution of N,N′-di-(p-anisyl)ethylenediamine diacetate (11.7 g) in water (40 mL) and isopropyl alcohol (40 mL) and stirred well at 25-30° C. After stirring for 2-3 hours, the reaction mixture was cooled to 5-10° C., filtered, washed with chilled water (0-5° C.) and isopropyl alcohol (0-5° C.) and dried the material under vacuum at ˜40° C. to get N,N′-di-(p-anisyl)ethylenediamine salt of 7-D-mandelamido-3-(((1-sulfomethyl-1H-tetrazol-5-yl)thio)methyl)-3-cephem-4-carboxylic acid (6.4 g). Step-(ii)

Aufarbeitung

  1. additionwas added at 0-5° C.
  2. customAfter the completion of reaction
  3. temperaturemaintained
  4. additionwas added
  5. stirringstirred well at 25-30° C
  6. stirringAfter stirring for 2-3 hours
  7. temperaturethe reaction mixture was cooled to 5-10° C.
  8. filtrationfiltered
  9. washwashed with chilled water (0-5° C.) and isopropyl alcohol (0-5° C.)
  10. customdried the material under vacuum at ˜40° C.

Quellen und Nachweise

ORD-Eintrag
ord-82464808ea184eac849c01f6e3428383
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741478B2

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