Phosphoric Acid → HCID 23707052, compound

HRID 326061Notes

Reaction equation

HRID 326061 reaction equation
C(OCC)(=O)C.[CH3:7][C@@:8]1([CH2:21][Cl:22])[S:12](=[O:14])(=[O:13])[C@@H:11]2[CH2:15][C:16](=[O:17])[N:10]2[C@H:9]1[C:18]([O-:20])=[O:19].[K+:23].[K].P(=O)(O)(O)O>O>[CH3:7][C@@:8]1([CH2:21][Cl:22])[S:12](=[O:14])(=[O:13])[C@@H:11]2[CH2:15][C:16](=[O:17])[N:10]2[C@H:9]1[C:18]([O-:20])=[O:19].[K+:23]

Participants

5

Reactant 3

HCID 1004Phosphoric AcidHCID 8857Ethyl AcetateHCID 86738498HCID 86738498, compound

Product 1

HCID 23707052HCID 23707052, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 25 ml of ethyl acetate and 10 ml of water was added 800 mg (0.00261 mole) of BL-P2013 potassium salt. After all of the solid had dissolved, the mixture was treated dropwise with 50% aqueous phosphoric acid with vigorous shaking until no more material precipitated from the aqueous layer. The ethyl acetate layer was separated, then washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and washed with 10 ml of ethyl acetate. (The wash solvent was combined with the original filtrate). "Skellysolve B" was then added to the ethyl acetate to the cloud point (approx. 10 ml). The mixture was treated with 500 mg of activated carbon ("Darko KB") and filtered. The filtrate was diluted with 15 ml of "Skellysolve B", then seeded with crystals of BL-P2013 free acid. After approx. 3 hours at room temperature, the crystalline precipitate of free acid was collected and dried in vacuo (15 min) over P 2 O5 to obtain 323 mg (46%) m.p. slow decomp. over 100°.

Workup

  1. dissolutionAfter all of the solid had dissolved
  2. customprecipitated from the aqueous layer
  3. customThe ethyl acetate layer was separated
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe drying agent was removed by filtration
  7. washwashed with 10 ml of ethyl acetate
  8. addition"Skellysolve B" was then added to the ethyl acetate to the cloud point (approx. 10 ml)
  9. additionThe mixture was treated with 500 mg of activated carbon ("Darko KB")
  10. filtrationfiltered
  11. additionThe filtrate was diluted with 15 ml of "Skellysolve B"
  12. customthe crystalline precipitate of free acid was collected
  13. customdried in vacuo (15 min) over P 2
  14. customto obtain 323 mg (46%)
  15. customover 100°

Sources & evidence

ORD record
ord-c3a99204066b4394bc3b323ed580df8d
Source dataset
uspto-grants-1984_04
Patent number
US04444687

Reaction notes

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