Hydrochloric Acid → HCID 131712745, compound

HRID 647241Notes

Reaction equation

HRID 647241 reaction equation
[CH2:1]([O:3][N:4]=[C:5]([C:29]1[N:33]=[C:32]([NH2:34])[S:31][N:30]=1)[C:6]([NH:8][CH:9]1[C:27](=[O:28])[N:11]2[C:12]([C:24]([OH:26])=[O:25])=[C:13]([CH2:16]OC(=O)CC(C)=O)[CH2:14][S:15][C@H:10]12)=[O:7])[CH3:2].C(=O)(O)[O-].[Na+].[I-].[K+].[C:42]([C:45]1[CH:50]=[CH:49][N:48]=[CH:47][CH:46]=1)(=[O:44])[NH2:43].Cl>O.C(OCC)(=O)C>[CH2:1]([O:3][N:4]=[C:5]([C:29]1[N:33]=[C:32]([NH2:34])[S:31][N:30]=1)[C:6]([NH:8][CH:9]1[C:27](=[O:28])[N:11]2[C:12]([C:24]([O-:26])=[O:25])=[C:13]([CH2:16][N+:48]3[CH:49]=[CH:50][C:45]([C:42](=[O:44])[NH2:43])=[CH:46][CH:47]=3)[CH2:14][S:15][C@H:10]12)=[O:7])[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 15074IsonicotinamideHCID 516892Sodium BicarbonateHCID 131712747HCID 131712747, compound

Product 1

HCID 131712745HCID 131712745, compoundYield 31.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-acetoacetoxymethyl-3-cephem-4-carboxylic acid (syn isomer) (14.2 g), sodium bicarbonate (2.33 g), potassium iodide (140 g) and 4-carbamoyl-pyridine (5.08 g) in water (140 ml) was stirred for 2.75 hours at 55° C. After cooling, ethyl acetate (100 ml) and 6 N hydrochloric acid were added thereto under stirring to adjust the PH of the mixture to 2. The aqueous layer was separated out, washed with ethyl acetate and concentrated under reduced pressure. An insoluble substance was filtered off and the filtrate was subjected to column chromatography on a non ionic adsorption resin, Diaion HP20 (300 ml). After the column was washed with water (500 ml), the elution was carried out with 30% aqueous methanol. The eluates containing an object compound were collected, evaporated to remove methanol under reduced pressure and lyophilized to give 7-[2-ethoxyimino-2-(5-amino-1,2,4-thiadiazol-3 -yl)acetamido]-3-(4-carbamoyl-1-pyridiniomethyl)-3-cephem-4-carboxylate (syn isomer) (4.7 g), mp 160° to 165° C.(dec.).

Workup

  1. temperatureAfter cooling
  2. stirringunder stirring
  3. customThe aqueous layer was separated out
  4. washwashed with ethyl acetate
  5. concentrationconcentrated under reduced pressure
  6. filtrationAn insoluble substance was filtered off
  7. washAfter the column was washed with water (500 ml)
  8. washthe elution
  9. additionThe eluates containing an object compound
  10. customwere collected
  11. customevaporated
  12. customto remove methanol under reduced pressure

Sources & evidence

ORD record
ord-d6fd3ce709544455b6824f553fc06e2e
Source dataset
uspto-grants-1983_10
Patent number
US04408042

Reaction notes

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