Sodium Bicarbonate → HCID 178483732, compound

HRID 28024Notes

Reaction equation

HRID 28024 reaction equation
[NH:1]=[C:2]1[NH:6][C:5]([CH2:7][C:8]([NH:10][C@@H:11]2[C:40](=[O:41])[N:13]3[C:14]([C:37]([OH:39])=[O:38])=[C:15](OC(=O)C4C=CC=CC=4S(=O)(=O)NC(OCC)=O)[CH:16](C)[S:17][C@H:12]23)=[O:9])=[CH:4][S:3]1.[SH:42][C:43]1[N:47]([CH2:48][CH2:49][N:50]([CH3:52])[CH3:51])[N:46]=[N:45][N:44]=1.[C:53](=O)([O-])O.[Na+]>O>[NH:1]=[C:2]1[NH:6][C:5]([CH2:7][C:8]([NH:10][C@@H:11]2[C:40](=[O:41])[N:13]3[C:14]([C:37]([OH:39])=[O:38])=[C:15]([CH2:53][S:42][C:43]4[N:47]([CH2:48][CH2:49][N:50]([CH3:52])[CH3:51])[N:46]=[N:45][N:44]=4)[CH2:16][S:17][C@H:12]23)=[O:9])=[CH:4][S:3]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 178473599HCID 178473599, compoundHCID 178483731HCID 178483731, compound

Product 1

HCID 178483732HCID 178483732, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In water (5 ml) are dissolved 7β-(2-imino-4-thiazolin-4-yl)acetamido-3-[2-(N-carboethoxysulfamoyl)benzoyloxy]-methyl-3-cephem-4-carboxylic acid (313 mg), 5-mercapto-1-[2-(N,N-dimethylamino)ethyl]-1H-tetrazole (113 mg) and sodium hydrogen carbonate (42 mg) and the resultant solution is heated at 55° C. for 60 minutes. The reaction solution is adjusted its pH to 5.8 and purified by column chromatography on Amberlite XAD-2 and the fractions rich in the desired product are pooled and lyophilized. The procedure provides 7β-(2-imino-4-thiazolin-4-yl)acetamido-3-{1-[2-(N,N-dimethylamino)ethyl]-1H-tetrazol-5-yl}thiomethyl-3-cephem-4-carboxylic acid.

Workup

  1. custompurified by column chromatography on Amberlite XAD-2

Sources & evidence

ORD record
ord-1069c6bf555444c59b2b22a15983855c
Source dataset
uspto-grants-1980_09
Patent number
US04224441

Reaction notes

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