Sodium hydride → HCID 53942722, compound

HRID 849588Notes

Reaction equation

HRID 849588 reaction equation
[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:18])[NH:12][C@H:13]([CH3:17])[C:14](O)=[O:15])[S:2]1.[S:19]([NH2:23])([NH2:22])(=[O:21])=[O:20].[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:18])[NH:12][C@H:13]([CH3:17])[C:14]([NH:22][S:19]([NH2:23])(=[O:21])=[O:20])=[O:15])[S:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 82267SulfamideHCID 53852971HCID 53852971, compound

Product 1

HCID 53942722HCID 53942722, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The reaction was carried out as described in Example 73, but using 0.21 g of 2(R)-{3-[4-(1,2-dithiolan-3-yl)butyl]ureido}propionic acid (prepared as described in Example 71), 5 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 ethyl acetate, to obtain 114 mg of the title compound as a pale yellow powder, melting at 156 to 157° 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 ethyl acetate

Sources & evidence

ORD record
ord-e16f022be68347bc8407e32e20fb7069
Source dataset
uspto-grants-2000_01
Patent number
US06013663

Reaction notes

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