Unsaturated lactones and mercaptans. Part III. Lactam of 2-(β-carboxyethyl)-2-methylthiazolidine-4-carboxylic acid from α-angelica lactone (pent-3-en-4-olide) and cysteine, and its n.m.r. spectrum
Journal of the Chemical Society C: Organic Pub Date: DOI: 10.1039/J39680000392
Abstract
The reaction product from α-angelica lactone (pent-3-en-4-olide) and cysteine was considered by Cavallito and Haskell to be an eight-membered ring lactam; Black has recently found supporting evidence for this. Reinvestigation by n.m.r., however, reveals the compound to be the lactam of 2-(β-carboxyethyl)-2-methylthiazolidine-4-carboxylic acid. The reaction proceeds in two steps and a mechanism leading to this unexpected structure is given. The identity between this compound and the one from 4-oxopentanoic acid and cysteine is demonstrated.
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Journal Name：Journal of the Chemical Society C: Organic
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CAS no.: 89640-58-4
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