(+-)-Penicillamine → 5,5-Dimethyl-2-(pyridin-3-yl)-1,3-thiazolidine-4-carboxylic acid

HRID 2210594Notes

Reaction equation

HRID 2210594 reaction equation
[NH2:1][CH:2]([C:7]([OH:9])=[O:8])[C:3]([SH:6])([CH3:5])[CH3:4].[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=O)[CH:11]=1>C(O)C>[N:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]2[NH:1][CH:2]([C:7]([OH:9])=[O:8])[C:3]([CH3:5])([CH3:4])[S:6]2)[CH:11]=1

Participants

4

Reactant 2

HCID 4727(+-)-PenicillamineHCID 103713-Pyridinecarboxaldehyde

Product 1

HCID 27377735,5-Dimethyl-2-(pyridin-3-yl)-1,3-thiazolidine-4-carboxylic acidYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of DL-penicillamine (50 g, 335 mmol) in 1:1 aqueous ethanol (500 mL) was added 3-pyridinecarboxaldehyde (36 g, 335 mmol). The resulting clear-yellow solution was stirred for 17 hours at ambient temperature during which time a white precipitate formed. The white solid was filtered off and rinsed with 3:1 H2O, ethanol and ether to give 2-(3-pyridinyl)-5,5-dimethyl-4-thiazolidinecarboxylic acid (51 g, 64%).

Workup

  1. customformed
  2. filtrationThe white solid was filtered off
  3. washrinsed with 3:1 H2O, ethanol and ether

Sources & evidence

ORD record
ord-909af57a0d16435899efdbf1c3cffb89
Source dataset
uspto-grants-1995_10
Patent number
US05459152

Reaction notes

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