Hydrochloric Acid → HCID 178480382, compound

HRID 1614092Notes

Reaction equation

HRID 1614092 reaction equation
Cl.FC(F)(F)C(O)=O.C([NH:11][C:12]1[S:13][CH:14]=[C:15]([C:17](=[N:40][O:41][CH:42]2[CH2:46][CH2:45][CH:44]=[CH:43]2)[C:18]([NH:20][C@@H:21]2[C:38](=[O:39])[N:23]3[C:24]([C:35]([O-:37])=[O:36])=[C:25]([CH2:28][N+:29]4[N:30]([CH3:34])[CH:31]=[CH:32][CH:33]=4)[CH2:26][S:27][C@H:22]23)=[O:19])[N:16]=1)=O.C(=O)(O)[O-].[Na+]>CO.O>[NH2:11][C:12]1[S:13][CH:14]=[C:15]([C:17](=[N:40][O:41][CH:42]2[CH2:46][CH2:45][CH:44]=[CH:43]2)[C:18]([NH:20][C@@H:21]2[C:38](=[O:39])[N:23]3[C:24]([C:35]([O-:37])=[O:36])=[C:25]([CH2:28][N+:29]4[N:30]([CH3:34])[CH:31]=[CH:32][CH:33]=4)[CH2:26][S:27][C@H:22]23)=[O:19])[N:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 178480381HCID 178480381, compound

Product 1

HCID 178480382HCID 178480382, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Conc. hydrochloric acid (4.1 g) was added to a solution of trifluoroacetic acid salt of 7β-[2-(2-formamidothiazol-4-yl)-2-(2-cyclopenten-1-yloxyimino)acetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (A isomer) (syn isomer) (5.8 g) in methanol (60 ml), and the mixture was stirred at ambient temperature for 2 hours. To the reaction mixture was added water (60 ml) and adjusted to pH 2.0 with 5% aqueous solution of sodium bicarbonate. The separated aqueous solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (120 ml) and eluted with 30% aqueous solution of methanol. The fractions containing the object compound were collected and concentrated in vacuo, then lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-(2-cyclopenten-1-yloxyimino)-acetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (A isomer) (syn isomer) (1.1 g).

Workup

  1. washeluted with 30% aqueous solution of methanol
  2. additionThe fractions containing the object compound
  3. customwere collected
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bd76ca851df045e99621499874ca3b78
Source dataset
uspto-grants-1993_03
Patent number
US05194432

Reaction notes

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