Sodium Hydroxide → 5-{[5-(1,2-Dithiolan-3-yl)pentanoyl]amino}pentanoic acid

HRID 849590Notes

Reaction equation

HRID 849590 reaction equation
[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[O:11])[S:2]1.[OH-].[Na+]>CO>[S:1]1[CH2:5][CH2:4][CH:3]([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:11])[S:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18357981HCID 18357981, compound

Product 1

HCID 183580775-{[5-(1,2-Dithiolan-3-yl)pentanoyl]amino}pentanoic acidYield 53.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The reaction was carried out as described in Example 49, but using 0.65 g of methyl 5-[5-(1,2-dithiolan-3-yl)pentanoylamino]pentanoate (prepared as described in Example 118), 13 ml of methanol and 5.09 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 0.33 g of the title compound as pale yellowish green crystals, melting at 98 to 100° 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-8d2393d226ea439e9541123c5f01307b
Source dataset
uspto-grants-2000_01
Patent number
US06013663

Reaction notes

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