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

HRID 248338Notes

Reaction equation

HRID 248338 reaction equation
[I-].C(OC([NH:9][C@@H:10]1[C:47](=[O:48])[N:12]2[C:13]([C:31]([O:33]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:32])=[C:14]([CH2:17][N+:18]3[N:19]([CH2:26][CH2:27][O:28][CH:29]=[O:30])[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:47](=[O:48])[N:12]2[C:13]([C:31]([O-:33])=[O:32])=[C:14]([CH2:17][N+:18]3[N:19]([CH2:26][CH2:27][O:28][CH:29]=[O:30])[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 10259694Benzhydryl 7beta-tert-butoxycarbonylamino-3-[3-formamido-2-(2-formyloxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate iodide

Product 1

HCID 149965697beta-Amino-3-[3-formamido-2-(2-formyloxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylateYield 153.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzhydryl 7β-tert-butoxycarbonylamino-3-[3-formamido-2-(2-formyloxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate iodide (29.5 g) and anisole (30 ml) in methylene chloride (90 ml) was added dropwise trifluoroacetic acid (60 ml) under ice-cooling. After being stirred for 1 hour at ambient temperature, the mixture was poured into a mixture of diisopropyl ether (600 ml) and ethyl acetate (600 ml). The resultant precipitate was collected by filtration to give di(trifluoroacetic acid) salt of 7β-amino-3-[3-formamido-2-(2-formyloxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate (22.7 g).

Workup

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

Sources & evidence

ORD record
ord-ac4b87aeb5d74b2d8db7dbe71bf7fbdb
Source dataset
uspto-grants-1993_05
Patent number
US05210080

Reaction notes

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