Trifluoroacetic acid → 7beta-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate

HRID 373430Notes

Reaction equation

HRID 373430 reaction equation
FC(F)(F)C(O)=O.Cl.Cl.Cl.[NH2:11][C:12]1[S:16][N:15]=[C:14]([C:17](=[N:41][O:42][C:43]([C:46]([O:48]C(C)(C)C)=[O:47])([CH3:45])[CH3:44])[C:18]([NH:20][C@@H:21]2[C:39](=[O:40])[N:23]3[C:24]([C:36]([O-:38])=[O:37])=[C:25]([CH2:28][N+:29]4[N:30]([CH3:35])[C:31]([NH2:34])=[CH:32][CH:33]=4)[CH2:26][S:27][C@H:22]23)=[O:19])[N:13]=1.C1(OC)C=CC=CC=1.C(OC(C)C)(C)C>C(Cl)Cl>[NH2:11][C:12]1[S:16][N:15]=[C:14]([C:17](=[N:41][O:42][C:43]([C:46]([OH:48])=[O:47])([CH3:44])[CH3:45])[C:18]([NH:20][C@@H:21]2[C:39](=[O:40])[N:23]3[C:24]([C:36]([O-:38])=[O:37])=[C:25]([CH2:28][N+:29]4[N:30]([CH3:35])[C:31]([NH2:34])=[CH:32][CH:33]=4)[CH2:26][S:27][C@H:22]23)=[O:19])[N:13]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 7914Diisopropyl EtherHCID 1317173227beta-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate trihydrochloride

Product 1

HCID 1317173247beta-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylateYield 20.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (7 ml) was added dropwise to a suspension of 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate trihydrochloride (3.3 g) and anisole (3.5 ml) in methylene chloride (10 ml) at ambient temperature. After being stirred at the same temperature for 4 hours, the mixture was poured into diisopropyl ether (300 ml), and the resulting precipitate was collected by filtration. The precipitate was dissolved in water (100 ml), and the solution was adjusted to pH 2 with 5% aqueous solution of sodium bicarbonate. The aqueous solution was 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 lyophilized to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-(3-amino-2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (syn isomer) (515 mg).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. dissolutionThe precipitate was dissolved in water (100 ml)
  3. washThe desired product was eluted with 5% aqueous isopropyl alcohol solution

Sources & evidence

ORD record
ord-e518d48ca9fc4c1192cda64ba171ce96
Source dataset
uspto-grants-1992_11
Patent number
US05162520

Reaction notes

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