Hydrochloric Acid → HCID 178480380, compound

HRID 1074353Notes

Reaction equation

HRID 1074353 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([O:11][N:12]=[C:13]([C:36]2[N:37]=[C:38]([NH:41]C=O)[S:39][CH:40]=2)[C:14]([NH:16][C@@H:17]2[C:34](=[O:35])[N:19]3[C:20]([C:31]([O-:33])=[O:32])=[C:21]([CH2:24][N+:25]4[N:26]([CH3:30])[CH:27]=[CH:28][CH:29]=4)[CH2:22][S:23][C@H:18]23)=[O:15])[CH2:10][CH2:9]1.Cl.C(OCC)C>CO>[NH2:41][C:38]1[S:39][CH:40]=[C:36]([C:13](=[N:12][O:11][CH:8]2[CH2:9][CH2:10]2)[C:14]([NH:16][C@@H:17]2[C:34](=[O:35])[N:19]3[C:20]([C:31]([O-:33])=[O:32])=[C:21]([CH2:24][N+:25]4[N:26]([CH3:30])[CH:27]=[CH:28][CH:29]=4)[CH2:22][S:23][C@H:18]23)=[O:15])[N:37]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 178480379HCID 178480379, compound

Product 1

HCID 178480380HCID 178480380, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of trifluoroacetic acid salt of 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (syn isomer, 2.35 g) in methanol (12 ml) was added conc. hydrochloric acid (0.8 ml) at ambient temperature, and the mixture was stirred at the same temperature for 2 hours. The reaction mixture was added to diethyl ether (300 ml), and the precipitates were collected by filtration. The precipitates were dissolved in water (20 ml) and the solution was adjusted to pH 5 with saturated aqueous solution of sodium bicarbonate. The solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark, manufactured by Mitsubishi Chemical Industries) and eluted with 15% aqueous solution of isopropyl alcohol. The fractions containing the object compound were collected and evaporated in vacuo to remove isopropyl alcohol. The solution was lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate (syn isomer, 0.68 g).

Workup

  1. filtrationthe precipitates were collected by filtration
  2. dissolutionThe precipitates were dissolved in water (20 ml)
  3. washeluted with 15% aqueous solution of isopropyl alcohol
  4. additionThe fractions containing the object compound
  5. customwere collected
  6. customevaporated in vacuo
  7. customto remove isopropyl alcohol

Sources & evidence

ORD record
ord-e3830b39faf04a5b8026eb95b6358c0b
Source dataset
uspto-grants-1990_11
Patent number
US04973699

Reaction notes

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