Hydrochloric Acid → HCID 131714298, compound

HRID 484817Notes

Reaction equation

HRID 484817 reaction equation
[S:1]1[CH2:4][CH:3]([O:5][N:6]=[C:7]([C:30]2[N:31]=[C:32]([NH:35]C=O)[S:33][CH:34]=2)[C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[C:14]([C:25]([O-:27])=[O:26])=[C:15]([CH2:18][N+:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH2:2]1.Cl>CO>[S:1]1[CH2:2][CH:3]([O:5][N:6]=[C:7]([C:30]2[N:31]=[C:32]([NH2:35])[S:33][CH:34]=2)[C:8]([NH:10][CH:11]2[C:28](=[O:29])[N:13]3[C:14]([C:25]([O-:27])=[O:26])=[C:15]([CH2:18][N+:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:16][S:17][C@H:12]23)=[O:9])[CH2:4]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131713228HCID 131713228, compound

Product 1

HCID 131714298HCID 131714298, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-[2-(3-thietanyloxyimino)-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (1.1 g) and conc. hydrochloric acid (0.8 g) in methanol (80 ml) was stirred at room temperature for 3 hours. Methanol was evaporated in vacuo and the residue was pulverized with isopropyl ether. The solid was dissolved in water (50 ml) and the solution was adjusted to pH 2.0 with 10% hydrochloric acid. The insoluble substance was filtered off. The filtrate was subjected to column chromatography on macroporous non-ionic adsorption resin "Diaion HP-20" (Trademark: prepared by Mitsubishi Chemical Industries) and eluted with 10% aqueous solution of isopropyl alcohol. The fractions containing the object compound were concentrated and lyophilized to give 7-[2-(3-thietanyloxyimino)-2-(2-aminothiazol-4-yl)-acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (0.45 g).

Workup

  1. customMethanol was evaporated in vacuo
  2. dissolutionThe solid was dissolved in water (50 ml)
  3. filtrationThe insoluble substance was filtered off
  4. custom" (Trademark: prepared by Mitsubishi Chemical Industries)
  5. washeluted with 10% aqueous solution of isopropyl alcohol
  6. additionThe fractions containing the object compound
  7. concentrationwere concentrated

Sources & evidence

ORD record
ord-a2df566ca0f448608ecf5d0dbae1fe4c
Source dataset
uspto-grants-1985_08
Patent number
US04533738

Reaction notes

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