Hydrochloric Acid → HCID 22467174, compound

HRID 1934754Notes

Reaction equation

HRID 1934754 reaction equation
C([O:5][C:6](=[O:31])[CH2:7][N:8]1[C:12]2([CH2:17][CH2:16][C:15](=[CH:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:14][CH2:13]2)[S:11][CH:10]([CH2:23][C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25])[C:9]1=[O:30])(C)(C)C.Cl>C(OCC)C.O1CCOCC1>[CH:27]([O:26][C:24](=[O:25])[CH2:23][CH:10]1[C:9](=[O:30])[N:8]([CH2:7][C:6]([OH:31])=[O:5])[C:12]2([CH2:13][CH2:14][C:15](=[CH:18][CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:16][CH2:17]2)[S:11]1)([CH3:29])[CH3:28]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid3×HCID 22467176Isopropyl 2-[4-[2-(tert-butoxy)-2-oxoethyl]-8-(3-methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-2-yl]-acetate

Product 1

HCID 22467174HCID 22467174, compoundYield 27.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent3×

Procedure

In 3 ml of diethyl ether was dissolved 0.33 g of isopropyl 2-[4-[2-(tert-butoxy)-2-oxoethyl]-8-(3-methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-2-yl]-acetate. Then, 1 ml of a 5.39 mol/L solution of dry hydrogen chloride in dioxane was added and the resulting mixture was stirred at the same temperature as above for 2 hours. Further, 1 ml of 5.39 mol/L solution of dry hydrogen chloride in dioxane was added and the resulting mixture was stirred for one hour, after which 3 ml of 5.39 mol/L solution of dry hydrogen chloride in dioxane was added and the resulting mixture was stirred for one hour. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography [eluent: chloroform]. Then, hexane was added, and the deposited crystal was collected by filtration. Thus, 0.08 g of 2-[2-(2-isopropoxy-2-oxoethyl)-8-(3-methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]-acetic acid was obtained as a colorless crystalline product.

Workup

  1. stirringthe resulting mixture was stirred for one hour
  2. stirringthe resulting mixture was stirred for one hour
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue was purified by column chromatography [eluent: chloroform]
  5. additionThen, hexane was added
  6. filtrationthe deposited crystal was collected by filtration

Sources & evidence

ORD record
ord-134a70e07dae457685ba66d679eff206
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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