Reaction of 3-(2-Oxocloalkyl)Propionic Acid and(R)-2-Thioxothiazolidine-4-carboxylic Ethyl Ester

Abstract

Abstract: he equimolar reaction of 3-(2-oxocyclohexyl)propionic acid or 3-(2-oxocy-clopentyl) propionic acid and(R)-2-thioxothiazolidine-4-carboxyli ethyl ester (1)with N-methyl-2-chloropyridium salt in the presence of triethylamine produced the corresponding op-tically active N-3-(2-oxocycloalkyl) propionyl-2-thioxothiazolidine-4-carboxylic ethyl ester(2_a) and N-3-(2-oxocyclopentyl)propionyl-2-thioazolidine-4-carboxylic ethyl ester(2_b).When the molar ratio of 3-(2-oxocyclohexyl)-propionic acid to compounds 1 is 2:1,2_a andS-excess 3-(2-oxocyclohexyl)propionic acid were obtained.When 2_a and 2_b react withracemic a-phenylethylamine(molar ratio 1:2),the photoactive compound N-3-(2-oxocyclo-hexyl)propionyl-α-phenylethylaine(5_a)or N-3-(2-oxocyclopentyl)propionyl-α-phenylethyla-mine(5_b)were obtained.

Key words: (R)-2-Thioxothiazolidine-4-carboxylic ethyl ester, N-3-(2-Oxocycloalkyl)propi-onyl-2-thioxothiazolidine-4-carboxylic ethyl ester, Cyclization, α-Phenylethylamine

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LI Ye-Zhi, TIAN Yan-Qing, HUANG Hua-Min. Reaction of 3-(2-Oxocloalkyl)Propionic Acid and(R)-2-Thioxothiazolidine-4-carboxylic Ethyl Ester[J]. Chem. J. Chinese Universities, 1996, 17(1): 94.

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Reaction of 3-(2-Oxocloalkyl)Propionic Acid and(R)-2-Thioxothiazolidine-4-carboxylic Ethyl Ester

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