Hydrochloric Acid → HCID 131713492, compound

HRID 325974Notes

Reaction equation

HRID 325974 reaction equation
[CH2:1]([O:4][N:5]=[C:6]([C:29]1[N:30]=[C:31]([NH:34]C=O)[S:32][CH:33]=1)[C:7]([NH:9][CH:10]1[C:27](=[O:28])[N:12]2[C:13]([C:24]([O-:26])=[O:25])=[C:14]([CH2:17][N+:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][S:16][C@H:11]12)=[O:8])[C:2]#[CH:3].Cl.O.[OH-].[Na+]>CO>[CH2:1]([O:4][N:5]=[C:6]([C:29]1[N:30]=[C:31]([NH2:34])[S:32][CH:33]=1)[C:7]([NH:9][CH:10]1[C:27](=[O:28])[N:12]2[C:13]([C:24]([O-:26])=[O:25])=[C:14]([CH2:17][N+:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:15][S:16][C@H:11]12)=[O:8])[C:2]#[CH:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 131713494HCID 131713494, compound

Product 1

HCID 131713492HCID 131713492, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 7-[2-(2-propynyloxyimino)-2-(2-formamidothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (11.2 g) and conc. hydrochloric acid (2.3 g) in methanol (80 ml) was stirred for 3 hours at ambient temperature. The reaction mixture was poured into water (120 ml) and adjusted to pH 3.5 with 10% aqueous solution of sodium hydroxide and washed with ethyl acetate. The aqueous layer was adjusted to pH 5.0 with 10% aqueous solution of sodium hydroxide. After removing the solvent under reduced pressure, the aqueous solution was adjusted to pH 4.0 with 10% aqueous hydrochloric acid under ice-cooling. The solution was subjected to column chlomatography 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 objected compound were concentrated and lyphylized to give 7-[2-(2-propynyloxyimino)-2-(2-aminothiazol-4-yl)acetamido]-3-(1-pyridiniomethyl)- 3-cephem-4-carboxylate (syn isomer) (5.3 g).

Workup

  1. washwashed with ethyl acetate
  2. customAfter removing the solvent under reduced pressure
  3. temperaturecooling
  4. custom" (Trademark: prepared by Mitsubishi Chemical Industries)
  5. washeluted with 10% aqueous solution of isopropyl alcohol
  6. additionThe fractions containing the objected compound
  7. concentrationwere concentrated

Sources & evidence

ORD record
ord-dcb237eea69b45378d71f87f59fd3179
Source dataset
uspto-grants-1984_04
Patent number
US04443444

Reaction notes

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