Trifluoroacetic acid → HCID 131716074, compound

HRID 1723602Notes

Reaction equation

HRID 1723602 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[CH:8]1([O:11][N:12]=[C:13]([C:52]2[N:53]=[C:54]([NH:57][CH:58]=[O:59])[S:55][CH:56]=2)[C:14]([NH:16][C@@H:17]2[C:50](=[O:51])[N:19]3[C:20]([C:34]([O:36]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:35])=[C:21]([CH2:24][N+:25]4[CH:30]=[CH:29][C:28]([C:31](=[O:33])[NH2:32])=[CH:27][CH:26]=4)[CH2:22][S:23][C@H:18]23)=[O:15])[CH2:10][CH2:9]1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>C1(OC)C=CC=CC=1.C(Cl)Cl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:8]1([O:11][N:12]=[C:13]([C:52]2[N:53]=[C:54]([NH:57][CH:58]=[O:59])[S:55][CH:56]=2)[C:14]([NH:16][C@@H:17]2[C:50](=[O:51])[N:19]3[C:20]([C:34]([O-:36])=[O:35])=[C:21]([CH2:24][N+:25]4[CH:30]=[CH:29][C:28]([C:31](=[O:33])[NH2:32])=[CH:27][CH:26]=4)[CH2:22][S:23][C@H:18]23)=[O:15])[CH2:9][CH2:10]1

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131716076HCID 131716076, compound

Product 2

HCID 6422Trifluoroacetic acidHCID 131716074HCID 131716074, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a suspension of benzhydryl 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(4-carbamoyl-1-pyridinio)methyl-3-cephem-4-carboxylate trifluoroacetate (syn isomer) (2.7 g) in a mixture of anisol (5 ml) and methylene chloride (10 ml) was added trifluoroacetic acid (10 ml) under ice-cooling. The mixture was stirred at the same temperature for 30 minutes. The mixture was poured into diisopropyl ether (800 ml) and the resulted precipitate was collected and dried over phosphorus pentoxide to give trifluoroacetic acid salt of 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(4-carbamoyl-1-pyridinio)methyl-3-cephem-4-carboxylate (syn isomer) (1.63 g).

Workup

  1. temperaturecooling
  2. customthe resulted precipitate was collected
  3. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-87c5afd23d9c45c3b5e12a11ae2433ab
Source dataset
uspto-grants-1989_08
Patent number
US04861769

Reaction notes

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