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ChemicalBook CAS DataBase List D-Penicillamine
52-67-5

D-Penicillamine synthesis

4synthesis methods
d-penicillamine can be synthesized in a multistep process that begins with heating isobutyraldehyde, pyridine, sulfur, and ammonia in benzene to form 5,5-dimethyl-2- isopropyl-?3-thiazoline. Treatment with hydrogen cyanide gives 4-cyano-5,5-dimethyl- 2-isopropylthiazolidine, which on acid hydrolysis gives d,l-penicillamine hydrochloride. Resolution is accomplished by conversion of the racemate to d,l-3-formyl- 2,2,5,5-tetramethylthiazolidine-4-carboxylic acid by treatment first with acetone, then with acetic formic anhydride. The enantiomers are separated in the usual manner, using, for example, l-lysine or d-(?)- threo-1-(4-nitrophenyl)-2-aminopropane-1,3- diol. Acidification liberates d-3-formyl- 2,2,5,5-tetramethylthiazolidine-4-carboxylic acid, which is hydrolyzed with hydrochloric acid to yield d-penicillamine hydrochloride. Neutralization with ethanolic triethylamine affords d-penicillamine.
D-Penicillamine synthesis
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Yield:52-67-5 47%

Steps:

20 Example 20
By substituting p-phenylenediamine for 2-naphthylamine in the above procedure, D-penicillamine was obtained in a yield of 47.0%.

References:

Taisho Pharmaceutical Co., Ltd. US4150240, 1979, A

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