Sodium Hydroxide → HCID 18358064, compound

HRID 849591Notes

Reaction equation

HRID 849591 reaction equation
[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:21])[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]C)=[O:18])[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:21])[NH:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[S:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18358053HCID 18358053, compound

Product 1

HCID 18358064HCID 18358064, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The reaction was carried out as described in Example 48, but using 0.30 g of methyl 5-{3-[4-(1,2-dithiolan-3-yl)butyl]ureido}pentanoate (prepared as described in Example 119), 10 ml of methanol and 3.14 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 0.23 g of the title compound as pale yellow crystals, melting at 125 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. 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-0c910048dc1040cb897edb40ad7a49d1
Source dataset
uspto-grants-2000_01
Patent number
US06013663

Reaction notes

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