Dichloromethane → Cephaloglycin

HRID 1834074Notes

Reaction equation

HRID 1834074 reaction equation
[CH3:1][C:2]([O:4][CH2:5][C:6]1[CH2:25][S:24][C@@H:9]2[C@H:10]([NH:13][C:14]([C@H:16]([NH2:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:15])[C:11](=[O:12])[N:8]2[C:7]=1[C:26]([OH:28])=[O:27])=[O:3].O.S([O-])([O-])(=O)=O.[Mg+2].C(Cl)Cl>C(N(CC)CC)C>[CH3:1][C:2]([O:4][CH2:5][C:6]1[CH2:25][S:24][C@@H:9]2[C@H:10]([NH:13][C:14]([C@H:16]([NH2:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:15])[C:11](=[O:12])[N:8]2[C:7]=1[C:26]([OH:28])=[O:27])=[O:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 7061048122202-75-1

Product 1

HCID 19150Cephaloglycin

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a suspension consisting of 4.23 g. of cephaloglycin monohydrate, 3.0 g. of anhydrous magnesium sulfate, and 70 ml. of methylene chloride are added 3.1 ml. of triethylamine and after stirring the mixture for one hour at room temperature, magnesium sulfate was filtered off to provide a triethylamine salt solution of cephaloglycin. To the solution was added dropwise a solution of nicotinoyl chloride N-oxide prepared by adding dropwise 0.73 ml. of thionyl chloride to a solution consisting of 1.39 g. of nicotinic acid N-oxide, 1.4 ml. of triethylamine, and 30 ml. of methylene chloride under ice-cooling followed by stirring for 1.5 hours. In this case, the pH of the reaction mixture was maintained at 8-9 by adding triethylamine.

Workup

  1. filtrationmagnesium sulfate was filtered off

Sources & evidence

ORD record
ord-53f06f6a2a0f4de68eb9ffbfcae2a0bb
Source dataset
uspto-grants-1978_01
Patent number
US04068074

Reaction notes

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