Acetone → HCID 131716388, compound

HRID 373436Notes

Reaction equation

HRID 373436 reaction equation
[I-].OC1C=CC=CC=1C=[N:6][C@@H:7]1[C:40](=[O:41])[N:9]2[C:10]([C:24]([O:26]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:25])=[C:11]([CH2:14][N+:15]3[N:16]([CH3:23])[C:17]([NH:20][CH:21]=[O:22])=[CH:18][CH:19]=3)[CH2:12][S:13][C@H:8]12.[ClH:46].CC(C)=O.C(OCC)(=O)C>C(Cl)Cl.C(O)=O>[ClH:46].[NH2:6][C@@H:7]1[C:40](=[O:41])[N:9]2[C:10]([C:24]([O-:26])=[O:25])=[C:11]([CH2:14][N+:15]3[N:16]([CH3:23])[C:17]([NH:20][CH:21]=[O:22])=[CH:18][CH:19]=3)[CH2:12][S:13][C@H:8]12

Participants

7

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 137225456HCID 137225456, compound

Product 1

HCID 131716388HCID 131716388, compoundYield 98.7%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of benzhydryl 7β-(2-hydroxybenzylideneamino)-3-(3-formamido-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate iodide (510 g) in methylene chloride (1275 ml) and formic acid (1275 ml) was added 35% hydrochloric acid (145 g) at 20°~25° C. The mixture was stirred for 1 hour at 20°~25° C. and added dropwise into the mixture of acetone (1020 ml) and ethyl acetate (2040 ml) at the same temperature. The resulting precipitate was collected by filtration and dried in vacuo to give the mixture (255.9 g) of 7β-amino-3-(3-formamido-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate hydrochloride and 7β-amino-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate hydrochloride. The mixture (255.9 g) was dissolved in methanol (1023.6 ml). To the solution was added 35% hydrochloric acid (66.6 g) and the mixture was stirred for 1 hour at 28°~30 ° C. The insoluble material was filtered off and washed with methanol (512 ml). The combined filtrates and washings were added dropwise into the mixture of acetone (2560 ml) and ethyl acetate (5120 ml) at 20°~25° C. The resulting precipitate was collected by filtration and dried in vacuo to give 7β-amino-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate hydrochloride.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-981310da773c450fa0d591d7147db032
Source dataset
uspto-grants-1992_11
Patent number
US05162520

Reaction notes

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