Ethanol → (3R)-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]decane-3-carboxylic acid

HRID 1934741Notes

Reaction equation

HRID 1934741 reaction equation
C(O)C.[CH:4]([C:7]1[CH:20]=[CH:19][C:10]([O:11][CH:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]2)=[CH:9][CH:8]=1)([CH3:6])[CH3:5].O.Cl.[NH2:23][C@H:24]([C:27]([OH:29])=[O:28])[CH2:25][SH:26].C([O-])(=O)C.[Na+]>O>[CH:4]([C:7]1[CH:20]=[CH:19][C:10]([O:11][CH:12]2[CH2:17][CH2:16][C:15]3([S:26][CH2:25][C@@H:24]([C:27]([OH:29])=[O:28])[NH:23]3)[CH2:14][CH2:13]2)=[CH:9][CH:8]=1)([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 702EthanolHCID 23462L-Cysteine hydrochloride monohydrateHCID 517045Sodium AcetateHCID 224671444-(4-Isopropylphenoxy)-1-cyclohexanone

Product 1

HCID 70156069(3R)-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]decane-3-carboxylic acidYield 54.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a solvent mixture consisting of 21 ml of ethanol and 9 ml of water were dissolved 3.10 g of 4-(4-isopropylphenoxy)-1-cyclohexanone, 2.35 g of L-cysteine hydrochloride monohydrate and 1.10 g of sodium acetate. The mixture was stirred at ambient temperature for 6 hours. The reaction mixture was concentrated under reduced pressure, and water and ethyl ether were added to the concentrate. The deposited crystal was collected by filtration, and there was obtained 2.45 g of (3R)-8-(4-isopropylphenoxy)-1-thia-4-azaspiro[4.5]decan-3-carboxylic acid as a colorless crystalline product.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and water and ethyl ether
  2. additionwere added to the concentrate
  3. filtrationThe deposited crystal was collected by filtration

Sources & evidence

ORD record
ord-7a3e02c9157c49828c2b4131da2f3189
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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