Hydrochloric Acid → HCID 22467123, compound

HRID 1934735Notes

Reaction equation

HRID 1934735 reaction equation
[CH3:1][CH:2]([CH3:12])[CH2:3][CH:4]=[C:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1.[NH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].[SH:26][CH2:27][C:28](O)=[O:29].Cl>C(OCC)(=O)C.O1CCOCC1>[CH3:1][CH:2]([CH3:12])[CH2:3][CH:4]=[C:5]1[CH2:10][CH2:9][C:8]2([S:26][CH2:27][C:28](=[O:29])[N:13]2[CH2:14][CH2:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:7][CH2:6]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1133Thioglycolic AcidHCID 1116164Benzyl 3-aminopropanoateHCID 11636865HCID 11636865, compound

Product 1

HCID 22467123HCID 22467123, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

In an atmosphere of nitrogen, 3.32 g of 4-(3-methylbutylidene)-1-cyclohexanone and 5.35 g of benzyl 3-aminopropionate were added to 35 ml of dioxane and stirred at ambient temperature for 30 minutes, after which 2.25 g of mercaptoacetic acid was added and the resulting mixture was stirred under reflux for 3 hours. The reaction mixture was poured into a mixture of ice water and ethyl acetate, 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, saturated aqueous solution of sodium hydrogen carbonate and saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by column chromatography (eluent: hexane:ethyl acetate=6:1) gave 4.36 g of benzyl 3-[8-(3-methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]-propionate as a light yellow oily product.

Workup

  1. stirringthe resulting mixture was stirred
  2. temperatureunder reflux for 3 hours
  3. customthe organic layer was separated
  4. washThe organic layer was washed successively with water, saturated aqueous solution of sodium hydrogen carbonate 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: hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-e50948ebc71542e9aa8286c632718f16
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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