Water → Cefixime

HRID 1470210

Reaktionsgleichung

Reaktionsgleichung von HRID 1470210
OC1C=CC=CC=1/C=[N:5]\[C@@H:6]1[C:13](=[O:14])[N:12]2[C@@H:7]1[S:8][CH2:9][C:10]([CH:27]=[CH2:28])=[C:11]2[C:15]([O:17]CC1C=CC(OC)=CC=1)=[O:16].O.CS(O[C:39](=[O:57])/[C:40](/[C:51]1[N:52]=[C:53]([NH2:56])[S:54][CH:55]=1)=[N:41]\[O:42][CH2:43][C:44]([O:46]C(C)(C)C)=[O:45])(=O)=O.ClCCl>C(OC)(C)(C)C>[NH2:56][C:53]1[S:54][CH:55]=[C:51](/[C:40](=[N:41]/[O:42][CH2:43][C:44]([OH:46])=[O:45])/[C:39]([NH:5][C@@H:6]2[C:13](=[O:14])[N:12]3[C@@H:7]2[S:8][CH2:9][C:10]([CH:27]=[CH2:28])=[C:11]3[C:15]([OH:17])=[O:16])=[O:57])[N:52]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6344DichloromethaneHCID 90407632HCID 90407632, VerbindungHCID 178436965HCID 178436965, Verbindung

Produkt 1

HCID 5362065Cefixime

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

A reactor is charged with (6R,7R)-4-methoxybenzyl 7-((Z)-(2-hydroxybenzylidene)amino)-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (1 eq), water (6-9 weight % relative to the Schiff base), (Z)-2-(2-aminothiazol-4-yl)-2-((2-(tert-butoxy)-2-oxoethoxy)imino)acetic methanesulfonic anhydride (2.5 eq) and dichloromethane (1.75 mL per gram of Schiff base). The mixture is stirred for three hours at room temperature, then added to methyl tertiary butyl ether over the course of 2-3 hours, resulting in the formation of a solid. The solid is filtered and the filter cake was washed with additional methyl tertiary butyl ether. The filtered solid is deprotected using conventional methods and dried under vacuum to yield the title compound.

Aufarbeitung

  1. customresulting in the formation of a solid
  2. filtrationThe solid is filtered
  3. washthe filter cake was washed with additional methyl tertiary butyl ether
  4. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3200251d10ad4b95b0010ee20297c9ed
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006421B2

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