Sodium hydride → HCID 18357989, compound

HRID 849586Notes

Reaction equation

HRID 849586 reaction equation
[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[S:2]1.[S:14]([NH2:18])([NH2:17])(=[O:16])=[O:15].[H-].[Na+]>C1(C)C=CC=CC=1.CN(C)C=O>[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([NH:17][S:14]([NH2:18])(=[O:16])=[O:15])=[O:13])[S:2]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 82267SulfamideHCID 226203646-(1,2-Dithiolan-3-yl)hexanoic acid

Product 1

HCID 18357989HCID 18357989, compoundYield 19.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

The reaction was carried out as described in Example 107, but using 5 ml of a solution of 1.6 mmol of 6(1,2-dithiolan-3-yl)hexanoic acid (prepared as described in Example 104) in toluene, 7 ml of anhydrous dimethylformamide, 308 mg of N,N'-carbonyldiimidazole, 365 mg of sulfamide and 83 mg of sodium hydride (as a 55% w/w dispersion in mineral oil). The solvent was removed from the reaction mixture by evaporation under reduced pressure, and water was added to the residue, after which it was extracted with ethyl acetate. The extraction solution was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate was removed from the extraction solution by evaporation under reduced pressure, and the residue was subjected to silica gel column chromatography, using 3:2 and 2:1 by volume mixtures of ethyl acetate and hexane as the eluent. The solvent was removed from the eluate by evaporation under reduced pressure, and the residue was recrystallized from a 1:2 by volume mixture of ethyl acetate and hexane, to obtain 92 mg of the title compound as pale yellow crystals, melting at 130 to 132° C.

Workup

  1. customThe solvent was removed from the reaction mixture by evaporation under reduced pressure, and water
  2. additionwas added to the residue
  3. extractionafter which it was extracted with ethyl acetate
  4. washThe extraction solution was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe ethyl acetate was removed from the extraction solution by evaporation under reduced pressure
  7. customThe solvent was removed from the
  8. customeluate by evaporation under reduced pressure
  9. customthe residue was recrystallized from a 1:2 by volume mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-6e1d75ad40574d8baa3da91999030e2f
Source dataset
uspto-grants-2000_01
Patent number
US06013663

Reaction notes

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