Water → HCID 178434797, compound

HRID 1088647Notes

Reaction equation

HRID 1088647 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][C:32]1[N:36]=[C:35]([SH:37])[S:34][N:33]=1.C(=O)([O-])O.[Na+:42].O>P([O-])([O-])([O-])=O.C(O)C>[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:35]4[S:34][N:33]=[C:32]([CH3:31])[N:36]=4)[CH2:17][S:18][C@H:13]23)=[O:10])=[CH:5][S:4]1.[Na+:42]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 178434798HCID 178434798, compoundHCID 178475887HCID 178475887, compound

Product 1

HCID 178434797HCID 178434797, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1061PhosphateSolvent

Conditions

Temperature
70 °C

Procedure

In 20 ml of phosphate buffer (0.2M, pH 6.4) there was dissolved 0.663 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 0.198 g of 3-methyl-1,2,4-thiadiazole-5-thiol and 0.252 g of sodium hydrogen carbonate and the mixture 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 and 20% ethanol in the order mentioned. The fractions containing the desired product were pooled and lyophilized. By the above procedure there was obtained 0.142 g of the captioned compound.

Sources & evidence

ORD record
ord-a70b652b4d3444e7982a82bfc6871ecd
Source dataset
uspto-grants-1990_10
Patent number
US04963542

Reaction notes

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