Trifluoroacetic acid → 7beta-Amino-3-(3-formamido-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate

HRID 1031197Notes

Reaction equation

HRID 1031197 reaction equation
[I-].C(OC([NH:9][C@@H:10]1[C:43](=[O:44])[N:12]2[C:13]([C:27]([O:29]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:28])=[C:14]([CH2:17][N+:18]3[N:19]([CH3:26])[C:20]([NH:23][CH:24]=[O:25])=[CH:21][CH:22]=3)[CH2:15][S:16][C@H:11]12)=O)(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>C(Cl)Cl.C(OCC)(=O)C>[NH2:9][C@@H:10]1[C:43](=[O:44])[N:12]2[C:13]([C:27]([O-:29])=[O:28])=[C:14]([CH2:17][N+:18]3[N:19]([CH3:26])[C:20]([NH:23][CH:24]=[O:25])=[CH:21][CH:22]=3)[CH2:15][S:16][C@H:11]12

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 10628738Benzhydryl 7beta-tert-butoxycarbonylamino-3-(3-formamido-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate iodide

Product 1

HCID 108068457beta-Amino-3-(3-formamido-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylateYield 168.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzhydryl 7β-tert-butoxycarbonylamino-3-(3-formamido-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate iodide (20.9 g) and anisole (20 ml) in methylene chloride (40 ml) was added dropwise trifluoroacetic acid (40 ml) under ice-cooling. After being stirred for 1.5 hours at ambient temperature, the mixture was poured into a mixture of diisopropyl ether (300 ml) and ethyl acetate (300 ml). The resultant precipitate was collected by filtration to give di(trifluoroacetic acid) salt of 7β-amino-3-(3-formamido-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (16.20 g).

Workup

  1. temperaturecooling
  2. filtrationThe resultant precipitate was collected by filtration

Sources & evidence

ORD record
ord-71325088a3a44c2cad32c123248cb4e3
Source dataset
uspto-grants-1992_04
Patent number
US05108997

Reaction notes

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