Réaction #216065

ord-024a9568ad134237a9a2313146b0c9f7

Équation de réaction

[Na]
sodium
COc1ccc(COC(=O)C2=C(CSc3nc4cn(C)ccc-4[n+]3C)CS[C@@H]3C(NC(=O)/C(=N\O[C@@H](C)C(=O)OC(c4ccccc4)c4ccccc4)c4csc(NC(c5ccccc5)(c5ccccc5)c5ccccc5)n4)C(=O)N23)cc1.O=C([O-])C(F)(F)F
p-methoxybenzyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-{(S)-1-diphenylmethoxycarbonylethoxyimino}acetamido]-3-(1,5-dimethylimidazolo[4,5-c]pyridinium-2-yl)thiomethyl-3-cephem-4-carboxylate trifluoroacetate
→
C[C@H](O/N=C(\C(=O)NC1C(=O)N2C(C(=O)[O-])=C(CSc3nc4cn(C)ccc-4[n+]3C)CS[C@H]12)c1csc(N)n1)C(=O)O
title compound
Rendement 52.5%
C[C@H](O/N=C(\C(=O)NC1C(=O)N2C(C(=O)[O-])=C(CSc3nc4cn(C)ccc-4[n+]3C)CS[C@H]12)c1csc(N)n1)C(=O)O
7-[(Z)-2-(2-aminothiazol-4-yl)-2-{(S)-1-carboxyethoxyimino}acetamido]-3-(1,5-dimethylimidazolo[4,5-c]pyridinium-2-yl)thiomethyl-3-cephem-4-carboxylate
Rendement 52.5%

Réactifs

[Na]
sodium
COc1ccc(COC(=O)C2=C(CSc3nc4cn(C)ccc-4[n+]3C)CS[C@@H]3C(NC(=O)/C(=N\O[C@@H](C)C(=O)OC(c4ccccc4)c4ccccc4)c4csc(NC(c5ccccc5)(c5ccccc5)c5ccccc5)n4)C(=O)N23)cc1.O=C([O-])C(F)(F)F
p-methoxybenzyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-{(S)-1-diphenylmethoxycarbonylethoxyimino}acetamido]-3-(1,5-dimethylimidazolo[4,5-c]pyridinium-2-yl)thiomethyl-3-cephem-4-carboxylate trifluoroacetate

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Autrethe reaction and purification

Mode opératoire

Using 334 mg of p-methoxybenzyl 7-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-{(S)-1-diphenylmethoxycarbonylethoxyimino}acetamido]-3-(1,5-dimethylimidazolo[4,5-c]pyridinium-2-yl)thiomethyl-3-cephem-4-carboxylate trifluoroacetate as a starting material, the reaction and purification were carried out in the same manner as in Example 1(b) to obtain 87 mg of the title compound in the form of a sodium salt in a yield of 51%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05464829uspto-grants-1995_11