Penicillamine → (3S)-8-(4-isopropylphenoxy)-2,2-dimethyl-1-thia-4-azaspiro[4.5]decane-3-carboxylic acid

HRID 1934743Notes

Reaction equation

HRID 1934743 reaction equation
[CH:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH:9]2[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[NH2:18][C@@H:19]([C:24]([OH:26])=[O:25])[C:20]([SH:23])([CH3:22])[CH3:21].C(OCC)(=O)C>C(O)C.O>[CH:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH:9]2[CH2:14][CH2:13][C:12]3([S:23][C:20]([CH3:22])([CH3:21])[C@H:19]([C:24]([OH:26])=[O:25])[NH:18]3)[CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 5852PenicillamineHCID 8857Ethyl AcetateHCID 224671444-(4-Isopropylphenoxy)-1-cyclohexanone

Product 1

HCID 70155800(3S)-8-(4-isopropylphenoxy)-2,2-dimethyl-1-thia-4-azaspiro[4.5]decane-3-carboxylic acidYield 68.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

In a mixture of 0.70 ml of ethanol and 0.30 ml of water were dissolved 0.30 g of 4-(4-isopropylphenoxy)-1-cyclohexanone and 0.21 g of D-penicillamine. The solution thus formed was stirred at ambient temperature for 4 hours. The reaction mixture was poured into a solvent mixture consisting of water and ethyl acetate, 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. Hexane was added to the residue, and the deposited crystal was collected by filtration. Thus, 0.32 g of (3S)-8-(4-isopropylphenoxy)-2,2-dimethyl-1-thia-4-azaspiro[4.5]decane-3-carboxylic acid was obtained as a colorless crystalline product.

Workup

  1. customThe solution thus formed
  2. additionThe reaction mixture was poured into a solvent mixture
  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. additionHexane was added to the residue
  8. filtrationthe deposited crystal was collected by filtration

Sources & evidence

ORD record
ord-d6ee92f98fee4f6598b7407baaf9e9a1
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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