Reaction #436741

Reaction equation

7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-[3-(formamidomethyl)-4,5,6,7-tetrahydro-1-pyrazolo[1,5-a]pyrimidinio]methyl-3-cephem-4-carboxylate

→

7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-(3-aminomethyl-4,5,6,7-tetrahydro-1-pyrazolo[1,5-a]pyrimidinio)methyl-3-cephem-4-carboxylate

Yield 38.6%

Solvents

hydrochloric acid

Conditions

Workup

1. 1
   OtherThe reaction mixture was purified by preparative HPLC utilizing ODS column
2. 2
   workup.ADDITIONThe eluate containing a desired product
3. 3
   Concentrationwas concentrated to about 30 ml in vacuo
4. 4
   Otherchromatographed on Diaion®
5. 5
   Wash(Mitsubishi Chemical Corporation) eluting with 30% aqueous 2-propanol
6. 6
   ConcentrationThe eluate was concentrated to about 30 ml in vacuo

Procedure

A solution of 7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-[3-(formamidomethyl)-4,5,6,7-tetrahydro-1-pyrazolo[1,5-a]pyrimidinio]methyl-3-cephem-4-carboxylate (130 mg) in 10% aqueous hydrochloric acid (4.36 ml) was stirred at room temperature for 6 hours. The reaction mixture was purified by preparative HPLC utilizing ODS column. The eluate containing a desired product was concentrated to about 30 ml in vacuo. The concentrate was adjusted to about pH 3 with concentrated hydrochloric acid and chromatographed on Diaion® HP-20 (Mitsubishi Chemical Corporation) eluting with 30% aqueous 2-propanol. The eluate was concentrated to about 30 ml in vacuo and lyophilized to give 7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-(3-aminomethyl-4,5,6,7-tetrahydro-1-pyrazolo[1,5-a]pyrimidinio)methyl-3-cephem-4-carboxylate (48 mg) as an amorphous solid.

Source