Sodium hydride → HCID 18357988, compound

HRID 849587Notes

Reaction equation

HRID 849587 reaction equation
[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:17])[NH:12][CH2:13][C:14](O)=[O:15])[S:2]1.[S:18]([NH2:22])([NH2:21])(=[O:20])=[O:19].[H-].[Na+]>CN(C)C=O>[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:17])[NH:12][CH2:13][C:14]([NH:21][S:18]([NH2:22])(=[O:20])=[O:19])=[O:15])[S:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 82267SulfamideHCID 18358014HCID 18358014, compound

Product 1

HCID 18357988HCID 18357988, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction was carried out as described in Example 73, but using 0.20 g of 3-[4-(1,2-dithiolan-3-yl)butyl]ureidoacetic acid (prepared as described in Example 48), 4 ml of anhydrous dimethylformamide, 0.13 g of N,N'-carbonyldiimidazole, 0.15 g of sulfamide and 0.04 g 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. The mixture was neutralized by the addition of 2 N aqueous hydrochloric acid, 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 recrystallized from a mixture of methanol and ethyl acetate, to obtain 76 mg of the title compound as yellow crystals, melting at 143 to 145° 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. additionThe mixture was neutralized by the addition of 2 N aqueous hydrochloric acid
  4. extractionafter which it was extracted with ethyl acetate
  5. washThe extraction solution was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe ethyl acetate was removed from the extraction solution by evaporation under reduced pressure
  8. customthe residue was recrystallized from a mixture of methanol and ethyl acetate

Sources & evidence

ORD record
ord-7f3c823de5644e91a4ff9e70886cce28
Source dataset
uspto-grants-2000_01
Patent number
US06013663

Reaction notes

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