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filingDate 1984-07-31-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 1986-10-07-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_13151fa1c8c2b6f0dbb1534c36979c4c
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publicationDate 1986-10-07-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber US-4616084-A
titleOfInvention Process for the preparation of 7-acylamino-3-hydroxy-cephem-4-carboxylic acids and 7-acylamino-3-hydroxy-1-dethia-1-oxacephem-4-carboxylic acids
abstract A process for the preparation of a 7-acylamino-3-hydroxy-2-cephem-4-carboxylic acid, 7-acylamino-3-hydroxy-1-dethia-1-oxa-3-cephem-4-carboxylic acid or derivative thereof of the general formula ##STR1## in which R 1 is hydrogen or optionally substituted alkyl, alkenyl, alkinyl, aralkyl, aryl, heteroaryl, heteroaralkyl, aryloxyalkyl, heteroaryloxyalkyl, alkoxyalkyl, arylthioalkyl, heteroarylthioalkyl, alkylthioalkyl, alkoxy, aryloxy, alkylthio or arylthio, n R 2 is hydrogen, a carboxy-protective group or a pharmaceutically useful ester radical, and n X is sulphur or oxygen, n which comprises: n (a) reacting a compound of the formula ##STR2## with (i) a compound of the formula ##STR3## in which R 2 and X have the abovementioned meaning and Y represents diazo (N 2 ) or hydrogen (H 2 ) in an inert solvent in the presence of a Lewis acid or proton acid catalyst, or n (ii) a compound of the formula n n HX--CH.sub.2 --C.tbd.C--COOR.sup.2 n n to form an intemediate compound having a triple bond, and hydrating the triple bond, the compounds thus obtained, for Y being hydrogen (H 2 )--(in case of Y=diazo (N 2 ) directly the compounds of general formula (2) are obtained) thereby to produce a compound of the formula ##STR4## (b) reacting such compound with an azide in a solvent in the presence of a base to give a compound of the formula ##STR5## (c) converting said compound to the desired product by (i) irradiation in an inert solvent, or n (ii) warming in the presence of a catalyst. n The end products are, or can be converted to, known β-lactam antibiotics.
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Total number of triples: 559.