C - Chemistry – Metallurgy – 07 – C
Patent
C - Chemistry, Metallurgy
07
C
C07C 321/06 (2006.01) C07C 233/08 (2006.01) C07C 319/06 (2006.01) C07C 319/24 (2006.01) C07C 335/32 (2006.01) C07D 307/94 (2006.01) C07C 323/53 (2006.01)
Patent
CA 2371048
A process for the preparation of highly pure 1-(mercaptomethyl)- cyclopropaneacetic acid is described. Treatment of 1-(hydroxymethyl)-cyclopropaneacetonitrile with an acid provides the corresponding imino ester and/or halo-amide, which when reacted with thiourea provide the corresponding amide-isothiuronium salt. Hydrolysis of the amide-isothiuronium salt followed by an in situ oxidation allows the facile isolation and purification of 1-[1-(carboxymethyl)-cyclopropanemethyldisulfanylmethyl]- cyclopropaneacetic acid (also known as 1-(mercaptomethyl)-cyclopropaneacetic acid disulfide). Reduction of the 1-(mercaptomethyl)-cyclopropaneacetic acid disulfide under mild conditions provides the 1-(mercaptomethyl)-cyclopropaneacetic acid with high purity.
On décrit un procédé pour la préparation d'acide 1-(mercaptométhyl)cyclopropaneacétique de pureté élevée. Le traitement de 1-(hydroxyméthyl)-cyclopropaneacétonitrile avec un acide produit l'iminoester correspondant et/ou l'haloamide correspondant, que l'on fait réagir avec de la thiourée pour obtenir le sel d'amide-isothiuronium correspondant. L'hydrolyse de ce sel, suivie d'une oxydation in situ, permet d'isoler et de purifier facilement l'acide 1-¬1-(carboxyméthyl)-cyclopropaneméthyldisulfanylméthyl|cyclopropaneacétique aussi appelé acide 1-(mercaptométhyl)cyclopropaneacétique disulfurique). La réduction de l'acide 1-(mercaptométhyl)cyclopropaneacétique disulfurique en conditions douces donne de l'acide 1-(mercaptométhyl)cyclopropaneacétique de pureté élevée.
Bydlinski Gregory
Harper Sylvain
Liu Lu Wei
Marrugo Herika
Quan David D.c.
Delmar Chemicals Inc.
Ridout & Maybee Llp
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