Sodium Acetate → (3S)-8-(3-methylbutylidene)-1-thia-4-azaspiro[4.5]decane-3-carboxylic Acid

HRID 2249664Notes

Reaction equation

HRID 2249664 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.O.Cl.[NH2:15][C@@H:16]([C:19]([OH:21])=[O:20])[CH2:17][SH:18].C([O-])(=O)C.[Na+]>C(O)C.O>[CH3:1][CH:2]([CH3:12])[CH2:3][CH:4]=[C:5]1[CH2:10][CH2:9][C:8]2([S:18][CH2:17][C@H:16]([C:19]([OH:21])=[O:20])[NH:15]2)[CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 10176341D-Cysteine hydrochloride monohydrateHCID 11636865HCID 11636865, compound

Product 1

HCID 68987170(3S)-8-(3-methylbutylidene)-1-thia-4-azaspiro[4.5]decane-3-carboxylic AcidYield 50%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

In a mixture of 3.5 ml of ethanol and 1.5 ml of water are dissolved 1.0 g of 4-(3-methylbutylidene)-1-cyclohexanone, 1.1 g of D-cysteine hydrochloride monohydrate and 0.52 g of sodium acetate. The resulting solution is stirred at ambient temperature for 2 hours. Water is added to the reaction mixture and the deposited crystal is collected by filtration. Thus, 0.81 g of (3S)-8-(3-methylbutylidene)-1-thia-4-azaspiro[4.5]decane-3-carboxylic acid is obtained as a colorless crystalline product.

Workup

  1. filtrationthe deposited crystal is collected by filtration

Sources & evidence

ORD record
ord-53da8030ee984247b476023849f61499
Source dataset
uspto-grants-2008_01
Patent number
US07314888B1

Reaction notes

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