Hydrochloric Acid → 7-Amino-3-(1-methyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate dihydrochloride

HRID 1607946Notes

Reaction equation

HRID 1607946 reaction equation
[NH2:1][CH:2]1[C:19](=[O:20])[N:4]2[C:5]([C:16]([O-:18])=[O:17])=[C:6]([CH2:9][N+:10]3([CH3:15])[CH2:14][CH2:13][CH2:12][CH2:11]3)[CH2:7][S:8][C@H:3]12.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:33].Cl.Cl>C(O)(C)C>[ClH:33].[ClH:33].[NH2:1][CH:2]1[C:19](=[O:20])[N:4]2[C:5]([C:16]([O-:18])=[O:17])=[C:6]([CH2:9][N+:10]3([CH3:15])[CH2:14][CH2:13][CH2:12][CH2:11]3)[CH2:7][S:8][C@H:3]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 1317151057-Amino-3-(1-methylpyrrolidinio)methyl-3-cephem-4-carboxylate

Product 1

HCID 1317161277-Amino-3-(1-methyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate dihydrochloride

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

To a suspension of 7-amino-3-(1-methyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate, dihydrochloride (9.8 g) in 1N-hydrochloric acid (39 ml) was added dropwise isopropyl alcohol (46 ml). After being stirred for 1 hour at room temperature, additional isopropyl alcohol (70 ml) was added thereto. The mixture was stirred for further 1 hour at the same temperature to give crystals. The crystals were collected by filtration, washed with isopropyl alcohol and diisopropyl ether and dried over phosphorus pentoxide to give crystalline 7-amino-3-(1-methyl-1-pyrrolidinio)methyl-3-cephem-4-carboxylate dihydrochloride.

Workup

  1. stirringThe mixture was stirred for further 1 hour at the same temperature
  2. customto give crystals
  3. filtrationThe crystals were collected by filtration
  4. washwashed with isopropyl alcohol and diisopropyl ether
  5. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-3ddbf9bee753460c9a7e56d5d393e7a4
Source dataset
uspto-grants-1989_09
Patent number
US04868174

Reaction notes

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