Hydrochloric Acid → HCID 88179563, compound

HRID 992699Notes

Reaction equation

HRID 992699 reaction equation
FC(F)(F)C(O)=O.FC(F)(F)C(O)=O.[NH2:15][C:16]1[S:17][CH:18]=[C:19](/[C:21](=[N:45]/[O:46]C(=O)C)/[C:22]([NH:24][C@@H:25]2[C:43](=[O:44])[N:27]3[C:28]([C:40]([OH:42])=[O:41])=[C:29]([S:32][CH2:33][C:34]4[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=4)[CH2:30][S:31][C@H:26]23)=[O:23])[N:20]=1.[Cl-].[NH4+].Cl>O.CO>[NH2:15][C:16]1[S:17][CH:18]=[C:19](/[C:21](=[N:45]/[OH:46])/[C:22]([NH:24][C@@H:25]2[C:43](=[O:44])[N:27]3[C:28]([C:40]([OH:42])=[O:41])=[C:29]([S:32][CH2:33][C:34]4[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=4)[CH2:30][S:31][C@H:26]23)=[O:23])[N:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 178476693HCID 178476693, compound

Product 1

HCID 88179563HCID 88179563, compoundYield 17.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(acetoxyimino)acetamido]-3-[(3-pyridyl)methylthio]-3-cephem-4-carboxylic acid bis(trifluoroacetic acid) salt (3.85 g, 5.05 m mol) and ammonium chloride (810 mg, 15.2 m mol) in a mixture of water (116 ml) and methanol (11.6 ml) was stirred at room temperature for 2.5 hours with keeping pH 8. The reaction mixture was adjusted to pH 6 by addition of 1N HCl. Methanol in the mixture was removed by evaporation in vacuo. The aqueous solution was adjusted to pH 5 and chromatographed on HP-20 (100 ml) and eluted with 5-10% aqueous isopropanol. The eluent was lyophilized. To the crude product was added water and acetonitrile. The precipitates were collected by filtration, washed with water and dried in vacuo to give 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(hydroxyimino)acetamido]-3-[(3-pyridyl)methyl-thio]-3-cephem-4-carboxylic acid (445 mg, 0.903 m mol).

Workup

  1. customMethanol in the mixture was removed by evaporation in vacuo
  2. customchromatographed on HP-20 (100 ml)
  3. washeluted with 5-10% aqueous isopropanol
  4. additionTo the crude product was added water and acetonitrile
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-838b769c00804000920b79123d7ae920
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

Loading…