Water → 3-[8-(3-Methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]-propionic acid

HRID 1934736Notes

Reaction equation

HRID 1934736 reaction equation
[CH3:1][CH:2]([CH3:28])[CH2:3][CH:4]=[C:5]1[CH2:27][CH2:26][C:8]2([S:12][CH2:11][C:10](=[O:13])[N:9]2[CH2:14][CH2:15][C:16]([O:18]CC2C=CC=CC=2)=[O:17])[CH2:7][CH2:6]1.[OH-].[Na+].C(Cl)(Cl)Cl.O>O1CCOCC1>[CH3:1][CH:2]([CH3:28])[CH2:3][CH:4]=[C:5]1[CH2:27][CH2:26][C:8]2([S:12][CH2:11][C:10](=[O:13])[N:9]2[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 22467123HCID 22467123, compound

Product 1

HCID 224671633-[8-(3-Methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]-propionic acidYield 85.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In 40 ml of dioxane was dissolved 4.11 g of benzyl 3-[8-(3-methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]-propionate. Then, 20.5 ml of 1 mol/L aqueous solution of sodium hydroxide was added at 0-5° C., and the resulting mixture was stirred at ambient temperature for one hour. The reaction mixture was poured into a mixture of chloroform and water, the aqueous layer was separated, ethyl acetate was added to the aqueous layer, pH was adjusted to 2.0 with 2 mol/L hydrochloric acid, and the organic layer was separated. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by column chromatography (eluent: chloroform:ethanol=50:1) gave 2.72 g of 3-[8-(3-methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]-propionic acid as a light yellow oily product.

Workup

  1. customthe aqueous layer was separated
  2. additionethyl acetate was added to the aqueous layer, pH
  3. customthe organic layer was separated
  4. washThe organic layer was washed successively with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customPurification of the residue by column chromatography (eluent: chloroform:ethanol=50:1)

Sources & evidence

ORD record
ord-10aa87732b034b128975ca395b074648
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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