Sodium Hydroxide → HCID 18358021, compound

HRID 849589Notes

Reaction equation

HRID 849589 reaction equation
[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:20])[NH:12][CH2:13][CH2:14][CH2:15][C:16]([O:18]C)=[O:17])[S:2]1.[OH-].[Na+]>CO>[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:20])[NH:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[S:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18357972HCID 18357972, compound

Product 1

HCID 18358021HCID 18358021, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The reaction was carried out as described in Example 48, but using 0.65 g of methyl 4-{3-[4-(1,2-dithiolan-3-yl)butyl]ureido}butanoate (prepared as described in Example 75), 13 ml of methanol and 7.10 ml of a 1 N aqueous solution of sodium hydroxide. 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 0.46 g of the title compound as a pale yellow powder, melting at 94 to 99° 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-1a242c25e20e4050a814efb299077a64
Source dataset
uspto-grants-2000_01
Patent number
US06013663

Reaction notes

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