Acetone → HCID 178478919, compound

HRID 1614072Notes

Reaction equation

HRID 1614072 reaction equation
[ClH:1].[I-:2].C(OC([NH:10][C@@H:11]1[C:41](=[O:42])[N:13]2[C:14]([C:25]([O:27]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:26])=[C:15]([CH2:18][N+:19]3[N:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)[CH2:16][S:17][C@H:12]12)=O)(C)(C)C.CC(C)=O.C(OCC)(=O)C>C(O)=O>[NH2:10][C@@H:11]1[C:41](=[O:42])[N:13]2[C:14]([C:25]([O-:27])=[O:26])=[C:15]([CH2:18][N+:19]3[N:20]([CH3:24])[CH:21]=[CH:22][CH:23]=3)[CH2:16][S:17][C@H:12]12.[ClH:1].[IH:2]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178480376HCID 178480376, compound

Product 1

HCID 178478919HCID 178478919, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Conc. hydrochloric acid (4.09 g) was added to a solution of benzhydryl 7β-tert-butoxycarbonylamino-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate iodide (27 g) in formic acid (108 ml), and stirred at ambient temperature for 2.5 hours. The reaction mixture was added to a mixture of acetone (720 ml) and ethyl acetate (1440 ml). The precipitates were collected by filtration and successively washed with ethyl acetate to give 7β-amino-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate·hydrochloride·hydroiodide (15.3 g).

Workup

  1. filtrationThe precipitates were collected by filtration
  2. washsuccessively washed with ethyl acetate

Sources & evidence

ORD record
ord-af82dd29c9cd4cffaccd08ab9e99107d
Source dataset
uspto-grants-1993_03
Patent number
US05194432

Reaction notes

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