Dichloromethane → Cephaloglycin

HRID 1834075Notes

Reaction equation

HRID 1834075 reaction equation
C(Cl)Cl.[CH3:4][C:5]([O:7][CH2:8][C:9]1[CH2:28][S:27][C@@H:12]2[C@H:13]([NH:16][C:17]([C@H:19]([NH2:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:18])[C:14](=[O:15])[N:11]2[C:10]=1[C:29]([OH:31])=[O:30])=[O:6].O.S([O-])([O-])(=O)=O.[Mg+2]>C(N(CC)CC)C>[CH3:4][C:5]([O:7][CH2:8][C:9]1[CH2:28][S:27][C@@H:12]2[C@H:13]([NH:16][C:17]([C@H:19]([NH2:26])[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:18])[C:14](=[O:15])[N:11]2[C:10]=1[C:29]([OH:31])=[O:30])=[O:6]

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

After stirring 35 ml. of a methylene chloride solution containing 2.12 g. of cephaloglycin monohydrate, 1.5 g. of anhydrous magnesium sulfate, and 1.4 ml. of triethylamine for one hour at room temperature, magnesium sulfate was filtered off to provide a solution of triethylamine salt of cephaloglycin. After cooling the solution to -25° C., 816 mg. of 2-imidazolidone-1-carboxylic acid chloride and further 0.3 ml. of triethylamine were added thereto.

Workup

  1. filtrationmagnesium sulfate was filtered off

Sources & evidence

ORD record
ord-30755719325545ef874dc2b560e95ab6
Source dataset
uspto-grants-1978_01
Patent number
US04068074

Reaction notes

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