Hydrochloric Acid → 2-[4-[3-(Benzyloxy)-3-oxopropyl]-8-(3-methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-2-yl]-acetic acid

HRID 1934734Notes

Reaction equation

HRID 1934734 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][CH:27]([CH2:31][C:32]([OH:34])=[O:33])[C:28](O)=[O:29].Cl>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][CH2:14][N:13]1[C:8]2([CH2:9][CH2:10][C:5](=[CH:4][CH2:3][CH:2]([CH3:12])[CH3:1])[CH2:6][CH2:7]2)[S:26][CH:27]([CH2:31][C:32]([OH:34])=[O:33])[C:28]1=[O:29])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6268(+-)-Mercaptosuccinic acidHCID 1116164Benzyl 3-aminopropanoateHCID 11636865HCID 11636865, compound

Product 1

HCID 224671502-[4-[3-(Benzyloxy)-3-oxopropyl]-8-(3-methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-2-yl]-acetic acidYield 59%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 20 ml of toluene were added 1.90 g of 4-(3-methylbutylidene)-1-cyclohexanone and 2.05 g of benzyl 3-aminopropionate, and the mixture was stirred at ambient temperature for one hour. Then, 1.72 g of mercaptosuccinic acid was added, and the resulting mixture was heated under reflux for one hour under the condition of azeotropic dehydration by means of Dean Stark. The reaction mixture was added to 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 and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue thus obtained was purified by column chromatography [eluent: chloroform:ethanol=50:1] to obtain 3.10 g of 2-[4-[3-(benzyloxy)-3-oxopropyl]-8-(3-methylbutylidene)-3-oxo-1-thia-4-azaspiro[4.5]decan-2-yl]-acetic acid as a light yellow oily product.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for one hour under the condition of azeotropic dehydration by means of Dean Stark
  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. customThe residue thus obtained
  8. customwas purified by column chromatography [eluent: chloroform:ethanol=50:1]

Sources & evidence

ORD record
ord-ce5c135664fd48cd88f2b7452942bd5b
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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