Water → HCID 178481307, compound

HRID 1088648Notes

Reaction equation

HRID 1088648 reaction equation
Cl.[NH:2]=[C:3]1[NH:7][C:6]([C:8](=[N:29][OH:30])[C:9]([NH:11][CH:12]2[C:27](=[O:28])[N:14]3[C:15]([C:24]([OH:26])=[O:25])=[C:16]([CH2:19]OC(=O)C)[CH2:17][S:18][C@H:13]23)=[O:10])=[CH:5][S:4]1.[CH3:31][N:32]1[CH:36]=[N:35][N:34]=[C:33]1[SH:37].C(=O)([O-])O.[Na+:42].O>P([O-])([O-])([O-])=O>[NH:2]=[C:3]1[NH:7][C:6]([C:8](=[N:29][OH:30])[C:9]([NH:11][CH:12]2[C:27](=[O:28])[N:14]3[C:15]([C:24]([O-:26])=[O:25])=[C:16]([CH2:19][S:37][C:33]4[N:32]([CH3:31])[CH:36]=[N:35][N:34]=4)[CH2:17][S:18][C@H:13]23)=[O:10])=[CH:5][S:4]1.[Na+:42]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 178475887HCID 178475887, compoundHCID 178481306HCID 178481306, compound

Product 1

HCID 178481307HCID 178481307, compound

Reagents, catalysts & solvents 1

HCID 1061PhosphateSolvent

Conditions

Temperature
70 °C

Procedure

In 20 ml of phosphate buffer (0.2M, pH 6.4) there was dissolved 0.883 g of 7-[2-(2-imino-4-thiazolin-4-yl)-2-hydroxyimino-acetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid hydrochloride (syn-isomer) together with 0.23 g of 4-methyl-1,2,4-triazole-3-thiol and 0.336 g of sodium hydrogen carbonate and the mixed solution was stirred at a temperature of 70° C. for 3.5 hours. The reaction mixture was subjected to column chromatography on polystyrene resin (Amberlite XAD-2, Rohm and Haas Co.), development being carried out with water. The fractions containing the desired product were pooled and lyophilized. By the above procedure there was obtained 0.371 g of the captioned compound.

Sources & evidence

ORD record
ord-9f22319e148e4e958aa75ffcf79abe6f
Source dataset
uspto-grants-1990_10
Patent number
US04963542

Reaction notes

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