http://rdf.ncbi.nlm.nih.gov/pubchem/patent/ES-2899606-T3

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filingDate 2005-03-24-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 2022-03-14-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_f7429ac2425c637f03855937e5c262dc
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publicationDate 2022-03-14-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber ES-2899606-T3
titleOfInvention Synthesis of ester compounds and boronic acids
abstract A process for forming a boronic acid anhydride of a compound of the formula (XIV): **(See formula)** comprising the steps: (A) coupling a trifluoroacetic acid addition salt of a compound of the formula ( XVIII): **(See formula)** with a compound of the formula (XIXa): **(See formula)** in which the moiety -C(O)X is an activated ester generated in situ by means of contact of N-(2-pyrazinocarbonyl)-L-phenylalanine with dicyclohexylcarbodiimide and N-hydroxysuccinimide, wherein the C(O)-X moiety is an O-(N-hydroxysuccinimide) ester, to form a compound of the formula ( XXIII): **(See formula)** and (B) deprotecting the boronic acid moiety to form a boronic acid anhydride of the compound of formula (XIV); wherein coupling step (A) comprises: (i) providing a solution of ammonium (1R)-(S)-pinandiol-1-trifluoroacetate-3-methylbutane-1-boronate and N-hydroxysuccinimide, followed by addition of dicyclohexylcarbodiimide to form a suspension; (ii) providing a solution of N-(2-pyrazinocarbonyl)-L-phenylalanine and adding N-methylmorpholine to it; (iii) adding the solution resulting from step ii) to the suspension resulting from step i) and, optionally, adjusting the resulting suspension to pH 7 by adding N-methylmorpholine; and wherein coupling step (A)(i) comprises providing a solution of (1R)-(S)-pinandiol-1-ammonium trifluoroacetate-3-methylbutane-1-boronate and N-hydroxysuccinimide in DMF, followed by the addition of dicyclohexylcarbodiimide to form a suspension; and/or coupling step (A)(ii) comprises providing a solution of N-(2-pyrazinecarbonyl)-L-phenylalanine in DMF and adding N-methylmorpholine thereto.
priorityDate 2004-03-30-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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