1-Methylpyrrolidine → 7-Benzoylamino-3-(1-methyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate

HRID 1607944Notes

Reaction equation

HRID 1607944 reaction equation
[C:1]([NH:9][CH:10]1[C:22](=[O:23])[N:12]2[C:13]([C:19]([OH:21])=[O:20])=[C:14]([CH2:17]Cl)[CH2:15][S:16][C@H:11]12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.C(OCC)(=O)C>O1CCCC1>[C:1]([NH:9][CH:10]1[C:22](=[O:23])[N:12]2[C:13]([C:19]([O-:21])=[O:20])=[C:14]([CH2:17][N+:25]3([CH3:24])[CH2:29][CH2:28][CH2:27][CH2:26]3)[CH2:15][S:16][C@H:11]12)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 84541-MethylpyrrolidineHCID 8857Ethyl AcetateHCID 678346777-Benzoylamino-3-chloromethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317161257-Benzoylamino-3-(1-methyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-benzoylamino-3-chloromethyl-3-cephem-4-carboxylic acid (14 g) in tetrahydrofuran (280 ml) was added dropwise 1-methylpyrrolidine (16.9 g) over a period of 10 minutes at 10° C. After the mixture was stirred for two hours at 25°~28° C., ethyl acetate (280 ml) was added thereto. The precipitate was collected by filtration, washed with ethyl acetate and diisopropyl ether, dried over phosphorus pentoxide to give 7-benzoylamino-3-(1-methyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with ethyl acetate and diisopropyl ether
  3. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-15e5f0b32c414f1883732d52ea6d2975
Source dataset
uspto-grants-1989_09
Patent number
US04868174

Reaction notes

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