HCID 141601005, compound → HCID 141601007, compound

HRID 349559Notes

Reaction equation

HRID 349559 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:37]/[O:38][C:39]([C:42]([OH:44])=[O:43])([CH3:41])[CH3:40])/[C:8]([NH:10][C@@H:11]2[C:35](=[O:36])[N:13]3[C:14]([C:32]([O-:34])=[O:33])=[C:15]([CH2:18][N+:19]4[N:23]5[CH2:24][CH2:25][CH2:26][NH:27][C:22]5=[C:21]([CH2:28][NH:29]C=O)[CH:20]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1>Cl>[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:37]/[O:38][C:39]([C:42]([OH:44])=[O:43])([CH3:40])[CH3:41])/[C:8]([NH:10][C@@H:11]2[C:35](=[O:36])[N:13]3[C:14]([C:32]([O-:34])=[O:33])=[C:15]([CH2:18][N+:19]4[N:23]5[CH2:24][CH2:25][CH2:26][NH:27][C:22]5=[C:21]([CH2:28][NH2:29])[CH:20]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1

Participants

3

Reactant 1

HCID 141601005HCID 141601005, compound

Product 1

HCID 141601007HCID 141601007, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

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.

Workup

  1. customThe reaction mixture was purified by preparative HPLC utilizing ODS column
  2. additionThe eluate containing a desired product
  3. concentrationwas concentrated to about 30 ml in vacuo
  4. customchromatographed on Diaion®
  5. wash(Mitsubishi Chemical Corporation) eluting with 30% aqueous 2-propanol
  6. concentrationThe eluate was concentrated to about 30 ml in vacuo

Sources & evidence

ORD record
ord-00966f5951e14feea7101aeed20cc7de
Source dataset
uspto-grants-2007_02
Patent number
US07179801B2

Reaction notes

Loading…