Hydrochloric Acid → HCID 88659219, compound

HRID 1979789Notes

Reaction equation

HRID 1979789 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:33])/[C:19](/[C:23]3[N:24]=[C:25]([NH:28][C:29](=[O:32])[CH2:30][Cl:31])[S:26][CH:27]=3)=[N:20]\[O:21][CH3:22])[C:15](=[O:34])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=O)C.C(=O)([O-])O.[Na+].[Cl-].[Ca+2].[Cl-].Cl>CO>[Cl:31][CH2:30][C:29]([NH:28][C:25]1[S:26][CH:27]=[C:23](/[C:19](=[N:20]/[O:21][CH3:22])/[C:18]([NH:17][CH:16]2[C:15](=[O:34])[N:10]3[C:11]([C:12]([OH:14])=[O:13])=[C:6]([CH2:5][O:4][CH3:1])[CH2:7][S:8][C@H:9]23)=[O:33])[N:24]=1)=[O:32]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5284359Calcium ChlorideHCID 12784203HCID 12784203, compound

Product 1

HCID 88659219HCID 88659219, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

5 g of 3-acetoxymethyl-7-[2-(2-chloroacetamidothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-3-cephem-4-carboxylic acid and 800 mg of sodium hydrogen carbonate were dissolved in 50 ml of 70% v/v aqueous methanol. 75 g of anhydrous calcium chloride were added to the solution, and the mixture was stirred at 70° C. for 1 hour. The mixture was then diluted with 100 ml of ice-water, acidified by the addition of 1 ml of concentrated hydrochloric acid, and extracted three times, each time with 100 ml of ethyl acetate. The extracts were combined and the combined extracts were extracted three times, each time with 50 ml of a 10% w/v aqueous solution of dipotassium phosphate. The extracts were combined and the combined extracts were washed with a small amount of ethyl acetate, acidified with a saturated aqueous solution of potassium hydrogen sulphate, and extracted twice with 100 ml portions of ethyl acetate and then once with 50 ml of ethyl acetate. The extracts were combined and the combined extracts were washed with an aqueous solution of sodium chloride, dehydrated over anhydrous magnesium sulphate and concentrated by evaporation under reduced pressure. When the volume of the mixture had reduced to about 50 ml, the evaporation was stopped, as crystals began to precipitate. The concentrate was first heated to redissolve the crystals and then ice-cooled and allowed to stand for 3 hours. The resulting crystals were collected by filtration, washed with ethyl acetate and dried, to give 3.01 g (yield 63.5%) of the title compound.

Workup

  1. extractionextracted three times
  2. extractionthe combined extracts were extracted three times
  3. washthe combined extracts were washed with a small amount of ethyl acetate
  4. extractionextracted twice with 100 ml portions of ethyl acetate
  5. washthe combined extracts were washed with an aqueous solution of sodium chloride
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customthe evaporation
  8. customto precipitate
  9. temperatureThe concentrate was first heated
  10. dissolutionto redissolve the crystals
  11. temperatureice-cooled
  12. waitto stand for 3 hours
  13. filtrationThe resulting crystals were collected by filtration
  14. washwashed with ethyl acetate
  15. customdried

Sources & evidence

ORD record
ord-96f10bab000b4e09a25dbec58570cf33
Source dataset
uspto-grants-1984_11
Patent number
US04482710

Reaction notes

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