Penicillamine → 5,5-Dimethyl-2-(3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridyl)-thiazolidine-4(S)-carboxylic acid

HRID 867416

Reaction equation

HRID 867416 reaction equation
[CH3:1][C:2]1[C:7]([OH:8])=[C:6]([CH:9]=O)[C:5]([CH2:11][OH:12])=[CH:4][N:3]=1.Cl.[NH2:14][C@@H:15]([C:20]([OH:22])=[O:21])[C:16]([SH:19])([CH3:18])[CH3:17].[OH-].[K+]>O>[CH3:17][C:16]1([CH3:18])[S:19][CH:9]([C:6]2[C:5]([CH2:11][OH:12])=[CH:4][N:3]=[C:2]([CH3:1])[C:7]=2[OH:8])[NH:14][C@H:15]1[C:20]([OH:22])=[O:21]

Participants

5

Reactant 3

HCID 5852PenicillamineHCID 6171Pyridoxal hydrochlorideHCID 14797Potassium Hydroxide

Product 1

HCID 127954745,5-Dimethyl-2-(3-hydroxy-5-hydroxymethyl-2-methyl-4-pyridyl)-thiazolidine-4(S)-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.03 g (10 mmoles) of pyridoxal hydrochloride are added to a solution containing 1.50 g (10 mmoles) of D-penicillamine and 0.56 g of potassium hydroxide in 10 ml of water. After stirring for 16 hours, the precipitate is filtered out to give the title acid in a yield of 2.26 g (75.7%) which can be purified by boiling with ethanol, m.p.: 201°-202° C., [α]D25 =+68.1°.

Workup

  1. filtrationthe precipitate is filtered out

Sources & evidence

ORD record
ord-7f7e1dd382244f3581e33359921ed1bb
Source dataset
uspto-grants-1988_10
Patent number
US04775675

Linked notes

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