Phthalimide potassium salt → HCID 11266194, compound

HRID 1368757Notes

Reaction equation

HRID 1368757 reaction equation
S([O:5][C@@H:6]([C@H:9](O)[CH2:10][Cl:11])[CH2:7][Cl:8])(O)(=O)=O.[K].[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12>CN(C=O)C>[Cl:8][CH2:7][C@@H:6]([OH:5])[C@@H:9]([N:18]1[C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]2[C:14]1=[O:24])[CH2:10][Cl:11]

Participants

4

Reactant 2

HCID 24194345Phthalimide potassium saltHCID 88104786HCID 88104786, compound

Product 1

HCID 11266194HCID 11266194, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1,4-dichlorobutan-2(S),3(S)-diol sulfate (57.2 mg, 0.258 mmol) and phthalimide potassium salt (51.4 mg, 0.272 mmol) in dry DMF (1.3 mL) was stirred under nitrogen atmosphere at rt for 1 h. Solvent was removed under reduced pressure. The residue was dissolved with dry THF (3 mL). To the resulting solution were added conc. H2SO4 (13 μl) and water (5 μl). After 30 min excess sodium bicarbonate (˜52 mg) was added and the reaction mixture was stirred for 30 min. Filtration through a Celite and silica gel bed and concentration of the filtrate under reduced pressure provided N-(1,4-Dichloro-2(S)-hydroxy-3(R)-butyl)phthalimide (77.8 mg) as a colorless oil.

Workup

  1. customSolvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved with dry THF (3 mL)
  3. additionTo the resulting solution were added conc. H2SO4 (13 μl) and water (5 μl)
  4. additionAfter 30 min excess sodium bicarbonate (˜52 mg) was added
  5. stirringthe reaction mixture was stirred for 30 min
  6. filtrationFiltration through a Celite and silica gel bed and concentration of the filtrate under reduced pressure

Sources & evidence

ORD record
ord-a88be25d88af44fba2129f1201e8c7c0
Source dataset
uspto-grants-2003_06
Patent number
US06573388B1

Reaction notes

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