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US 4,363,920 AGranted
Process for the preparation of N-[2-(-thenoyl)thiopropionyl]-glycine
AssigneeB.T.B. Industria Chimica S.p.A.
InventorRenzo Viscardi
Life of this patent
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Abstract
N-[2-(2-thenoyl)thiopropionyl]-glycine is prepared, according to a process which is especially advantageous for the purity and the stability of the product, by means of N-acylation of glycine with an activated derivative of 2-(2-thenoyl)thiopropionic acid.
Claims4
Process for the preparation of N-glycine (I) of formula:
- ##STR4## which consists of reacting glycine (III) with 2-(2-thenoyl)thiopropionic acid (II) of formula ##STR5## in the presence of N,N'-dicyclohexyl-carbodiimide at a temperature of 15.degree.-20.degree. C. in an aprotic solvent whereby said compound of formula (II) is converted in situ into the compound of formula (VI) ##STR6## and the compound of formula (VI) reacts with glycine, then removing the solvent, adding water, making the reaction mixture basic, removing dicyclohexyl urea by filtration and isolating said product of formula (I) by acidification.
Process for the preparation of N-glycine (I) of formula:
- ##STR7## which consists of reacting 2-(2-thenoyl)thiopropionic acid (II) of formula ##STR8## with a compound (IV) capable of converting said compound of formula (II) into a compound of formula (V) ##STR9## in which R is C.sub.1 -C.sub.4 alkyl, in the presence of a tertiary amine, then reacting with glycine at a temperature lower than 20.degree. C. and isolating the compound of formula (I) from the reaction mixture.
Process for the preparation of N-glycine (I) of formula:
- ##STR10## which consists of reacting 2-(2-thenoyl)thiopropionic acid (II) of formula ##STR11## with thionyl chloride at a temperature lower than 30.degree. C. and dissolving the acid chloride of said compound (II) thus formed in an anhydrous solvent to form a solution of the acid chloride of said compound II, and reacting said solution with glycine in the presence of an acid acceptor and isolating said compound of formula (I) from the reaction mixture.
Dependencies are inferred from the claim text.