Hydrochloric Acid → 7-[2-Ethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate

HRID 1163881Notes

Reaction equation

HRID 1163881 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:28]1[N:29]=[C:30]([NH:33]C=O)[S:31][CH:32]=1)[C:6]([NH:8][CH:9]1[C:26](=[O:27])[N:11]2[C:12]([C:23]([O-:25])=[O:24])=[C:13]([CH2:16][N+:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:14][S:15][C@H:10]12)=[O:7])[CH3:2].Cl.O.C(OCC)(=O)C>CO>[CH2:1]([O:3][N:4]=[C:5]([C:28]1[N:29]=[C:30]([NH2:33])[S:31][CH:32]=1)[C:6]([NH:8][CH:9]1[C:26](=[O:27])[N:11]2[C:12]([C:23]([O-:25])=[O:24])=[C:13]([CH2:16][N+:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:14][S:15][C@H:10]12)=[O:7])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 1317129237-[2-Ethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate

Product 1

HCID 1317129277-[2-Ethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylateYield 26.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-[2-ethoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (1.4 g) in methanol (20 ml) and conc. hydrochloric acid (0.85 g) were stirred for 2.5 hours at room temperature. The reaction mixture was added to a mixture of water and ethyl acetate. The aqueous layer was separated, washed with ethyl acetate and adjusted to pH 4.0 with 10% aqueous solution of sodium hydroxide. The resulting solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark: prepared by Mitsubishi Chemical Industries) and eluted with 5% aqueous solution of isopropyl alcohol. The fractions containing the object compound were concentrated and lyophilized to give 7-[2-ethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (0.35 g).

Workup

  1. customThe aqueous layer was separated
  2. washwashed with ethyl acetate
  3. customThe resulting solution was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark: prepared by Mitsubishi Chemical Industries)
  4. washeluted with 5% aqueous solution of isopropyl alcohol
  5. additionThe fractions containing the object compound
  6. concentrationwere concentrated

Sources & evidence

ORD record
ord-be13d760b20842599ba1d0e75ac9a5db
Source dataset
uspto-grants-1983_01
Patent number
US04367228

Reaction notes

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