Trifluoroacetic acid → HCID 131716628, compound

HRID 1614086Notes

Reaction equation

HRID 1614086 reaction equation
Cl.Cl.Cl.[NH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:34][O:35][CH2:36][C:37]([O:39]C(C)(C)C)=[O:38])[C:11]([NH:13][C@@H:14]2[C:32](=[O:33])[N:16]3[C:17]([C:29]([O-:31])=[O:30])=[C:18]([CH2:21][N+:22]4[N:23]([CH3:28])[C:24]([NH2:27])=[CH:25][CH:26]=4)[CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>C1(OC)C=CC=CC=1.C(Cl)Cl>[NH2:4][C:5]1[S:6][CH:7]=[C:8]([C:10](=[N:34][O:35][CH2:36][C:37]([OH:39])=[O:38])[C:11]([NH:13][C@@H:14]2[C:32](=[O:33])[N:16]3[C:17]([C:29]([O-:31])=[O:30])=[C:18]([CH2:21][N+:22]4[N:23]([CH3:28])[C:24]([NH2:27])=[CH:25][CH:26]=4)[CH2:19][S:20][C@H:15]23)=[O:12])[N:9]=1

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7914Diisopropyl EtherHCID 131716630HCID 131716630, compound

Product 1

HCID 131716628HCID 131716628, compoundYield 14.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a suspension of 7β-[2-(2-aminothiazol-4-yl)-2-tert-butoxycarbonylmethoxyiminoacetamido]-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate trihydrochloride (syn isomer) (1.2 g) in anisole (1.2 ml) and methylene chloride (3.6 ml) was added dropwise trifluoroacetic acid (2.4 ml) under ice-cooling. After being stirred at ambient temperature for 3 hours, the mixture was added dropwise to isopropyl ether (200 ml). The resultant precipitate was collected by filtration. The precipitate was dissolved in water (30 ml) and the solution was adjusted to pH 2 with 5% aqueous sodium bicarbonate solution, and then subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20". The desired product was eluted with 5% aqueous isopropyl alcohol solution, and isopropyl alcohol was evaporated. The aqueous layer was lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-carboxymethoxyiminoacetamido]-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (syn isomer) (131.3 mg).

Workup

  1. temperaturecooling
  2. filtrationThe resultant precipitate was collected by filtration
  3. dissolutionThe precipitate was dissolved in water (30 ml)
  4. washThe desired product was eluted with 5% aqueous isopropyl alcohol solution, and isopropyl alcohol
  5. customwas evaporated

Sources & evidence

ORD record
ord-e4775f23f2b44d9a98be1adcd0e1c902
Source dataset
uspto-grants-1993_03
Patent number
US05194432

Reaction notes

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