公开(公告)号：EP1474386B1

公开(公告)日：2006-12-27

申请号：EP03737225.7

申请日：2003-02-05

申请人： Delmar Chemicals Inc.

发明人： LIU, Lu, Wei ,  WANG, Yuan ,  MARRUGO, Herika ,  HARPER, Sylvain ,  QUAN, David, D. C. ,  ZHOU, Zhihong (Nancy) ,  BYDLINSKI, Gregory

IPC分类号： C07C319/06 ,  C07C319/24 ,  C07C233/08 ,  C07D307/94 ,  C07C323/53

CPC分类号： C07D307/94

摘要： 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 provides 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.

公开(公告)号：EP1474386A1

公开(公告)日：2004-11-10

申请号：EP03737225.7

申请日：2003-02-05

申请人： Delmar Chemicals Inc.

发明人： LIU, Lu, Wei ,  WANG, Yuan ,  MARRUGO, Herika ,  HARPER, Sylvain ,  QUAN, David, D. C. ,  ZHOU, Zhihong (Nancy) ,  BYDLINSKI, Gregory

IPC分类号： C07C319/06 ,  C07C319/24 ,  C07C233/08 ,  C07D307/94 ,  C07C323/53

CPC分类号： C07D307/94

摘要： 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 provides 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.