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The produce methods of Cefpirome

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The produce methods of Cefpirome

Post  rihanna on Wed Jul 27, 2011 10:43 pm

Cefpirome (CAS NO.84957-29-9) is a white to yellowish white crystalline powder, slight specific smell. More easily soluble in water and not very dissolve in ethanol or ether. For the treatment of sepsis and severe urinary tract infections, respiratory tract infections. Production methods can through active compounds (Ⅲ) and compounds (Ⅳ) to get.

Cefpirome(CAS NO.: 84957-29-9), with systematic name of 5H-1-Pyrindinium, 1-((7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-2-carboxy-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-en-3-yl)methyl)-5,6,7,8-tetrahydro-, hydroxide, inner salt, (6R-(6alpha,7beta(Z)))-, could be produced through many synthetic methods.

One of the reaction routes is as below:
The protection of 7-aminocephalosporanic acid (I) with di-tert-butyl dicarbonate gives 7-(tert-butoxycarbonylamino)cephalosporanic acid (II), which is condensed with 2,3-cyclopentenopyridine (III) by means of KI and NaHCO3 in hot water affording 7-(tert-butoxycarbonylamino)-3-[(2,3-cyclopenteno-1-pyridinium)methyl]ceph-3-em-4-carboxylate (IV). Deprotection of (IV) with trifluoroacetic acid anisole gives 7-amino-3-[(2,3-cyclopenteno-1-pyridinium)methyl]ceph-3-em-4-carboxylate (V), which is finally condensed with 2-(2-aminothiazol-4-yl)-2-syn-methoxyiminoacetic acid (VI) by means of phosgene in toluene.


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