Monobasic potassium phosphate → HCID 77769638, compound

HRID 343330Notes

Reaction equation

HRID 343330 reaction equation
P([O-])(O)(O)=O.[K+].[CH2:7]([O:9][C:10]([CH:12]1[CH2:17][C:16]([CH2:18][CH3:19])=[CH:15][CH2:14][N:13]1C(OCC(Cl)(Cl)[Cl:25])=O)=[O:11])[CH3:8]>O1CCCC1.[Zn]>[ClH:25].[CH2:7]([O:9][C:10]([CH:12]1[CH2:17][C:16]([CH2:18][CH3:19])=[CH:15][CH2:14][NH:13]1)=[O:11])[CH3:8]

Participants

5

Reactant 2

HCID 516951Monobasic potassium phosphateHCID 76454556HCID 76454556, compound

Product 1

HCID 77769638HCID 77769638, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 8028TetrahydrofuranSolvent

Procedure

1M Aqueous potassium dihydrogen phosphate solution (70 ml, 70 mmol), then zinc dust (46 g, 700 mmol), were added to a rapidly stirred solution of the product from (b) above (4.76 g, 13.3 mmol) in tetrahydrofuran (220 ml). After 2 hours at room temperature more zinc dust (5 g, 76 mmol) was added and the reaction mixture stirred for a further hour before being filtered. The filter pad was washed with water and tetrahydrofuran, then the bulk of the organic solvent removed from the combined filtrate and washings. The residual mixture was acidified with 2M hydrochloric acid (30 ml), washed with ethyl acetate to remove starting material (2.32 g recovered), neutralised with solid potassium carbonate and extracted with dichloromethane. The combined organic extracts were washed with saturated brine, dried (MgSO4), treated with excess ethereal hydrogen chloride and evaporated under reduced pressure. Purification of the residue by chromatography on silica gel, using dichloromethane:methanol (95:5) as eluent, furnished the title compound (330 mg), as a colourless waxy solid. m/e 184 (M+H)+.

Workup

  1. filtrationbefore being filtered
  2. washThe filter pad was washed with water and tetrahydrofuran
  3. customthe bulk of the organic solvent removed from the combined filtrate and washings
  4. washwashed with ethyl acetate
  5. customto remove
  6. custommaterial (2.32 g recovered)
  7. extractionextracted with dichloromethane
  8. washThe combined organic extracts were washed with saturated brine
  9. dry with materialdried (MgSO4)
  10. additiontreated with excess ethereal hydrogen chloride
  11. customevaporated under reduced pressure
  12. customPurification of the residue by chromatography on silica gel

Sources & evidence

ORD record
ord-53ce98ef9dcd41868a2b0fa04e90f549
Source dataset
uspto-grants-1999_01
Patent number
US05861393

Reaction notes

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