Reaction of 3-(2-oxocycloalkyl)propionic acid and (R)-2-thioxothiazolidine-4-carboxylic ethyl ester

Ye Zhi Li; Yan Qing Tian; Hua Min Huang

Reaction of 3-(2-oxocycloalkyl)propionic acid and (R)-2-thioxothiazolidine-4-carboxylic ethyl ester

Ye Zhi Li, Yan Qing Tian, Hua Min Huang

Research output: Contribution to journal › Article › peer-review

Abstract

The equimolar reaction of 3-(2-oxocyclohexyl) propionic acid or 3-(2-oxocyclopentyl) 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 optically active W-3-CZ-oxocycloalkyl) propionyl-2-thioxothiazolidine-4-carboxylic ethyl ester (2.) 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, and S-excess 3-(2-oxocyclohexyl) propionic acid were obtained. When 2_n and 2_b react with racemic α-phenylethylamine(molar ratio 1 : 2), the photoactive compound N-3-(2-oxocyclohexyl)propionyl-α-phenylethylaine(N_n) or N-3-(2-oxocyclopentyl)propionyl-a-phenylethylamine(5_b) were obtained.

Original language	English (US)
Pages (from-to)	X25-96
Journal	Kao Teng Hsueh Hsiao Hua Heush Hsueh Pao/ Chemical Journal of Chinese Universities
Volume	17
Issue number	1
State	Published - Dec 1 1996

Keywords

(R)-2-Thioxothiazolidine-4-carboxylic ethyl ester
Cyclization
N-3-(2-Oxocycloalkyl)propionyl-2-thioxothiazolidine-4-carboxylic ethyl ester
α-Phenylethylamine

ASJC Scopus subject areas

General Chemistry

Cite this

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title = "Reaction of 3-(2-oxocycloalkyl)propionic acid and (R)-2-thioxothiazolidine-4-carboxylic ethyl ester",

abstract = "The equimolar reaction of 3-(2-oxocyclohexyl) propionic acid or 3-(2-oxocyclopentyl) 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 optically active W-3-CZ-oxocycloalkyl) propionyl-2-thioxothiazolidine-4-carboxylic ethyl ester (2.) and N-3-(2-oxocyclopentyl) propionyl-2-thioazolidine-4-carboxylic ethyl ester (2b). When the molar ratio of 3-(2-oxocyclohexyl)-propionic acid to compounds 1 is 2 : 1. 2, and S-excess 3-(2-oxocyclohexyl) propionic acid were obtained. When 2n and 2b react with racemic α-phenylethylamine(molar ratio 1 : 2), the photoactive compound N-3-(2-oxocyclohexyl)propionyl-α-phenylethylaine(Nn) or N-3-(2-oxocyclopentyl)propionyl-a-phenylethylamine(5b) were obtained.",

keywords = "(R)-2-Thioxothiazolidine-4-carboxylic ethyl ester, Cyclization, N-3-(2-Oxocycloalkyl)propionyl-2-thioxothiazolidine-4-carboxylic ethyl ester, α-Phenylethylamine",

author = "Li, {Ye Zhi} and Tian, {Yan Qing} and Huang, {Hua Min}",

year = "1996",

month = dec,

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language = "English (US)",

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pages = "X25--96",

journal = "Kao Teng Hsueh Hsiao Hua Heush Hsueh Pao/ Chemical Journal of Chinese Universities",

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publisher = "Higher Education Press",

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TY - JOUR

T1 - Reaction of 3-(2-oxocycloalkyl)propionic acid and (R)-2-thioxothiazolidine-4-carboxylic ethyl ester

AU - Li, Ye Zhi

AU - Tian, Yan Qing

AU - Huang, Hua Min

PY - 1996/12/1

Y1 - 1996/12/1

N2 - The equimolar reaction of 3-(2-oxocyclohexyl) propionic acid or 3-(2-oxocyclopentyl) 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 optically active W-3-CZ-oxocycloalkyl) propionyl-2-thioxothiazolidine-4-carboxylic ethyl ester (2.) and N-3-(2-oxocyclopentyl) propionyl-2-thioazolidine-4-carboxylic ethyl ester (2b). When the molar ratio of 3-(2-oxocyclohexyl)-propionic acid to compounds 1 is 2 : 1. 2, and S-excess 3-(2-oxocyclohexyl) propionic acid were obtained. When 2n and 2b react with racemic α-phenylethylamine(molar ratio 1 : 2), the photoactive compound N-3-(2-oxocyclohexyl)propionyl-α-phenylethylaine(Nn) or N-3-(2-oxocyclopentyl)propionyl-a-phenylethylamine(5b) were obtained.

AB - The equimolar reaction of 3-(2-oxocyclohexyl) propionic acid or 3-(2-oxocyclopentyl) 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 optically active W-3-CZ-oxocycloalkyl) propionyl-2-thioxothiazolidine-4-carboxylic ethyl ester (2.) and N-3-(2-oxocyclopentyl) propionyl-2-thioazolidine-4-carboxylic ethyl ester (2b). When the molar ratio of 3-(2-oxocyclohexyl)-propionic acid to compounds 1 is 2 : 1. 2, and S-excess 3-(2-oxocyclohexyl) propionic acid were obtained. When 2n and 2b react with racemic α-phenylethylamine(molar ratio 1 : 2), the photoactive compound N-3-(2-oxocyclohexyl)propionyl-α-phenylethylaine(Nn) or N-3-(2-oxocyclopentyl)propionyl-a-phenylethylamine(5b) were obtained.

KW - (R)-2-Thioxothiazolidine-4-carboxylic ethyl ester

KW - Cyclization

KW - N-3-(2-Oxocycloalkyl)propionyl-2-thioxothiazolidine-4-carboxylic ethyl ester

KW - α-Phenylethylamine

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JF - Kao Teng Hsueh Hsiao Hua Heush Hsueh Pao/ Chemical Journal of Chinese Universities

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Reaction of 3-(2-oxocycloalkyl)propionic acid and (R)-2-thioxothiazolidine-4-carboxylic ethyl ester

Abstract

Keywords

ASJC Scopus subject areas

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