Process for preparing alpha-amino-phenylacetic acid-trifluoromethane sulfonic acid mixed anhydrides

{
  "publication_number": "US5338868A",
  "country": "US",
  "kind": "A",
  "title": "Process for preparing alpha-amino-phenylacetic acid-trifluoromethane sulfonic acid mixed anhydrides",
  "abstract": "A process is disclosed for the preparation of a compound of the Formula (VI) ##STR1## wherein X is a hydrogen atom, or OH, Y is a hydrogen atom, OH or a methyl group, R 2 is a CH--COOR group, or a group of the formula (XI) ##STR2## and R is a C 1 to C 2 alkyl group, which comprises the step of: reacting a condensed salt of the Formula (IV) ##STR3## wherein Me is Na + or K +, with a reactive derivative of trifluoromethane-sulfonic acid of the Formula (V) F.sub.3 C--SO.sub.2 OH. The compounds of the Formula (VI) are intermediates in the preparation of penicillins and cephalosporins with antibiotic activity.",
  "claims": [
    "1. A process for the preparation of a compound of the Formula (VI) ##STR13## wherein X is a hydrogen atom or OH; Y is a hydrogen atom, OH or a methyl group; R 2 is a CH--COOR group, where R is a C 1 to 2 alkyl group, or R 2 is a group of the Formula (XI) ##STR14## wherein a condensed salt of the Formula (IV) ##STR15## wherein Me is a sodium or potassium cation, is reacted with a reactive derivative of trifluoromethane-sulfonic acid of the Formula (V) F.sub.3 C--SO.sub.2 OH (V).",
    "2. Process according to claim 1, wherein the condensed salt is reacted with the trifluoromethane-sulphonic acid-chloride at a temperature of 0°-5° C.",
    "3. The process defined in claim 1 wherein the compound of the Formula (VI) is selected from the group consisting of: D(-)-N-(2-methoxycarbonyl-1-methyl-vinyl)-alpha-amino-(p-hydroxy-phenyl)-acetic acid-trifluoromethane sulfonic acid anhydride; and D(-)-N-(1-methyl-2-(2'-oxo-tetrahydro-furan-3'-yl)-vinyl)-alpha-amino-(p-hydroxyphenyl)-acetic acid-trifluoromethane sulfonic acid anhydride.",
    "4. The process defined in claim 1 wherein the compound of the Formula (VI) is D(-)-N-(1-methyl-2-(2'-oxo-tetrahydro-furan-3'-yl)-vinyl)-alpha-amino-(p-hydroxyphenyl)-acetic acid-trifluoromethane sulfonic acid anhydride."
  ],
  "description_excerpt": "The present invention relates to new valuable intermediates suitable for the acylation of 6-aminopenicillanic acids and 7-cephalosporanic acid in the production of pharmaceutical compositions. The present invention further provides a process for the preparation of said intermediate compounds and an improved process to prepare the known Dane salts.\n\nThe substituents in the formulae set forth herein are as follows:\n\nX stands for hydrogen or OH,\n\nY stands for hydrogen, OH or methyl,\n\nR stands for a C 1-2 alkyl group,\n\nA stands for hydrogen, Me of SO 2 CF 3, wherein Me stands for potassium or sodium ion\n\nR 1 stands for CH 2 --COOR or a group of the formula (IX) ##STR4## R 2 stands for CH--COOR or a group of formula (XI) ##STR5## The present invention relates to a process for preparing a compound of the formula (I) ##STR6## starting from an amino acid salt of the formula (II) ##STR7## by forming a salt by reacting phenylglycine of the formula (VII) ##STR8## with 1.05-1.3 mole of alkalihydroxide in the presence of an alkanol and by reacting the reaction mixture with an acid having a pH value higher than 4.3 and by using 1.06-1.4 mole equivalent acid related to phenylglycine, the excess of alkali-hydroxide can be dissolved more selectively, while the amino acid salt of the formula (II) precipitates from the solution or by reacting the reaction mixture with an equivalent amount of alkali salts of the acids having a pH-value above 4.3 and by condensing the amino acid salt of the ...",
  "cpc": [
    "C07D 307/58",
    "C07C 227/18",
    "C07C 229/36",
    "C07C 309/00"
  ],
  "ipc": [
    "C07C 227/18",
    "C07C 229/36",
    "C07C 309/00",
    "C07D 307/58"
  ],
  "assignees": [
    "Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt"
  ],
  "inventors": [
    "Karoly Ban",
    "Annamaria Ban",
    "Lajosne Pali",
    "Marta Kruppa",
    "Eva Somfai",
    "Csaba Huszar"
  ],
  "filing_date": "1991-05-24",
  "publication_date": "1994-08-16",
  "grant_date": "1994-08-16",
  "priority_date": "1989-07-27",
  "application_number": "US-68982891-A",
  "family_id": "10965648",
  "cited_by_count": 4,
  "citations": [
    "US3518260A",
    "EP0009609A2",
    "US4994572A"
  ]
}