Sodium Bicarbonate → HCID 131720147, compound

HRID 1376421Notes

Reaction equation

HRID 1376421 reaction equation
Cl.[NH2:2][C@@H:3]1[C:23](=[O:24])[N:5]2[C:6]([C:20]([O-:22])=[O:21])=[C:7]([CH2:10][N+:11]3[N:12]([CH2:17][CH2:18][OH:19])[C:13]([NH2:16])=[CH:14][CH:15]=3)[CH2:8][S:9][C@H:4]12.C(=O)(O)[O-].[Na+].Cl.[NH2:31][C:32]1[S:36][N:35]=[C:34](/[C:37](=[N:41]/[O:42][CH2:43][CH3:44])/[C:38](Cl)=[O:39])[N:33]=1>C(#N)C.O>[NH2:31][C:32]1[S:36][N:35]=[C:34]([C:37](=[N:41][O:42][CH2:43][CH3:44])[C:38]([NH:2][C@@H:3]2[C:23](=[O:24])[N:5]3[C:6]([C:20]([O-:22])=[O:21])=[C:7]([CH2:10][N+:11]4[N:12]([CH2:17][CH2:18][OH:19])[C:13]([NH2:16])=[CH:14][CH:15]=4)[CH2:8][S:9][C@H:4]23)=[O:39])[N:33]=1

Participants

6

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 15575214HCID 15575214, compoundHCID 118856010HCID 118856010, compound

Product 1

HCID 131720147HCID 131720147, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
5 °C

Procedure

A solution of 7β-amino-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate hydrochloride (50 g) in a mixture of acetonitrile (500 ml) and water (500 ml) was adjusted to pH 6.0 with aqueous sodium bicarbonate solution. To the resulting solution was added (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetyl chloride hydrochloride (40 g) under stirring at 5° C. and the mixture was stirred at the same temperature for 1.5 hours, keeping pH 5.0-6.5 with aqueous sodium bicarbonate solution. The reaction mixture was evaporated to remove the containing organic solvent. The water solution was subjected to column chromatography on Sepabeads SP-205 (Trademark: Mitsubishi Kasei Corporation) (1.3 l). The column was washed with water (5 l) and the object compound was eluted with 15% isopropyl alcohol, and the eluate was lyophilized to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido]-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate (syn isomer) (51.2 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 1.5 hours
  2. customThe reaction mixture was evaporated
  3. customto remove the containing organic solvent
  4. washThe column was washed with water (5 l)
  5. washthe object compound was eluted with 15% isopropyl alcohol

Sources & evidence

ORD record
ord-dd792c10b85147b79b52f476c0d8d690
Source dataset
uspto-grants-1997_09
Patent number
US05663163

Reaction notes

Loading…