Hydrochloric Acid → HCID 131714677, compound

HRID 280510Notes

Reaction equation

HRID 280510 reaction equation
[CH2:1]([O:4][N:5]=[C:6]([C:27]1[N:31]=[C:30]([NH2:32])[S:29][N:28]=1)[C:7]([NH:9][CH:10]1[C:25](=[O:26])[N:12]2[C:13]([C:22]([O-:24])=[O:23])=[C:14]([CH2:17]OC(=O)C)[CH2:15][S:16][C@H:11]12)=[O:8])[CH:2]=[CH2:3].[Na+].[CH3:34][N:35]1[C:39]2[CH2:40][CH2:41][CH2:42][C:38]=2[CH:37]=[N:36]1.[I-].[Na+].P(=O)(O)(O)O.Cl>O.C(#N)C>[CH2:1]([O:4][N:5]=[C:6]([C:27]1[N:31]=[C:30]([NH2:32])[S:29][N:28]=1)[C:7]([NH:9][CH:10]1[C:25](=[O:26])[N:12]2[C:13]([C:22]([O-:24])=[O:23])=[C:14]([CH2:17][N+:36]3[N:35]([CH3:34])[C:39]4[CH2:40][CH2:41][CH2:42][C:38]=4[CH:37]=3)[CH2:15][S:16][C@H:11]12)=[O:8])[CH:2]=[CH2:3]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1004Phosphoric AcidHCID 5238Sodium IodideHCID 13576584HCID 13576584, compoundHCID 131714679HCID 131714679, compound

Product 1

HCID 131714677HCID 131714677, compoundYield 18.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A mixture of sodium 7-[2-allyloxyimino-2-(5-amino-1,2,4-thiadiazole-3-yl)acetamido]-3-acetoxymethyl-3-cephem-4-carboxylate (syn isomer)(6.43 g), 1-methyl-5,6-dihydro-1H,4H-cyclopenta[c]pyrazole (3.2 g), sodium iodide (20.54 g), phosphoric acid (0.67 g), water (2.8 ml) and acetonitrile (8.5 ml) was stirred at 70° to 75° C. for 2 hours. The reaction mixture was poured into water (100 ml) and the aqueous layer was adjusted to pH 2.0 with 10% hydrochloric acid. After removal of precipitates by filtration, the aqueous solution was washed with ethyl acetate four times. The aqueous layer was adjusted to pH 2.5 with 5% aqueous solution of sodium bicarbonate and subjected to column chromatography on macroporous non-ionic adsorption resin Diaion HP-20 (Trademark : prepared by Mitsubishi Chemical Industries). The column was washed with water and eluted with 50% aqueous methanol. The fractions containing the object compound were combined and methanol was evaporated under reduced pressure. The resultant aqueous solution was lyophilized to give 7-[2-allyloxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)-acetamido]-3-[1-methyl-5,6-dihydro-2(1H,4H)-cyclopenta[c]pyrazolio]methyl-3-cephem-4-carboxylate (syn isomer)(1.3 g).

Workup

  1. customAfter removal
  2. customof precipitates by filtration
  3. washthe aqueous solution was washed with ethyl acetate four times
  4. custom(Trademark : prepared by Mitsubishi Chemical Industries)
  5. washThe column was washed with water
  6. washeluted with 50% aqueous methanol
  7. additionThe fractions containing the object compound
  8. custommethanol was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e23e9c8bf6134afb9a1a3e7753a42e0a
Source dataset
uspto-grants-1986_05
Patent number
US04590186

Reaction notes

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