http://rdf.ncbi.nlm.nih.gov/pubchem/patent/AR-035353-A1
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_05a203d85ee01909eaf728dc16f0f6cb |
| classificationCPCAdditional | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C2601-14 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07B2200-07 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C67-303 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07C67-343 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07F1-06 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C67-343 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C67-303 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C67-30 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07B53-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07F1-06 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C69-618 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C51-41 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07B61-00 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C69-612 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07C69-608 |
| filingDate | 2001-10-12-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 2004-05-12-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | AR-035353-A1 |
| titleOfInvention | OLEFINATION PROCEDURE TO PRODUCE ITACONATE AND SUCCINATE DERIVATIVES |
| abstract | An efficient and selective process, capable of being scaled up, to manufacture itaconate derivatives of formula (1) and / or succinate derivatives of formula (2) and / or (3) by asymmetric hydrogenation of itaconate derivatives in which R is aryl, C3-8 cycloalkyl, C1-10 alkyl, (aryl) C1-10 alkylene, (C3-8 cycloalkyl) C1-10 alkylene, heterocyclyl, (heterocyclyl) C1-10 alkylene, (aryl) C3-8 cycloalkylene , (C3-8 cycloalkyl) arylene or (C1-10 alkylaryl) C1-10 alkylene, being `` aryl '' a mono- or bicyclic carbocyclic ring system, partially or totally unsaturated, containing from 4 to 10 atoms, such as phenyl or naphthyl, or a mono- or bicyclic heterocyclic moiety, partially or totally unsaturated, having up to 10 atoms in the ring system and with up to 4 heteroatoms in said ring system independently selected from N, O and S, said being carbocyclic ring system and said heterocyclic moiety optionally substituted with one or more substituents each independently selected from halogen, NO2, NH2, CO2R9, phenyl, C1-6 alkyl (optionally substituted with one or more halogens) and C1-6 alkoxy (optionally substituted with one or more halogens), and being '' heterocyclyl ' 'a saturated heterocyclic group, mono- or bicyclic, of 3 to 8 members, having 1 to 4 ring heteroatoms each independently selected from N, O and S, optionally substituted with one or more substituents each independently selected from halogen , NO2, NH2, CO2R9, phenyl, C1-6 alkyl (optionally substituted with one or more halogens) and C1-6 alkoxy (optionally substituted with one or more halogens); R1 is C1-6 alkoxy; R2 is OH or O-M +; R9 is H or C1-6 alkyl; and M + is the cation of a metal such as sodium, lithium or potassium, or is a protonated amine moiety such as (mono-, di or tri-C 1-10 alkyl) ammonium, (mono-, di- or tri-cycloalkyl C3 -10) ammonium, (C1-10 alkyl) n1 (C3-10 cycloalkyl) n2 ammonium, anilinium, benzylammonium, triethanolammonium or (S) -alpha-methylbenzylammonium, in which each n1 and n2 is independently selected from 1 or 2, with the proviso that the sum of n1 and n2 is not greater than 3, characterized in that it comprises: the formation of a compound of formula (1) as defined above, by reaction of an aldehyde of formula RCHO, or a protected derivative thereof such as a hemiacetal or an adduct thereof such as a bisulfite, where R is as defined above, with a phosphorus compound of formula (4) or a metal carboxylate salt thereof, such as a sodium carboxylate salt, lithium or potassium thereof, wherein R1 is as defined above, and `` P '' is a phosphonate moiety of formula -P (O) (OR3) (O R4), each of R3 and R4 being independently selected from H, C1-6 alkyl, benzyl and phenyl (optionally substituted with one or more C1-6 alkyl moieties), or R3 and R4 taken together are C2-5 alkylene; or '' P '' is a phosphorane moiety of formula - (PR5R6R7) + X-, each being selected from R5, R6 and R7 independently from C1-6 alkyl and phenyl, and X being bromine, chlorine or iodine, in the presence of a C1-6 alkoxide base of sodium, lithium or potassium, in an inert solvent, and at a temperature of -80 ° C to 20 ° C, said process being optionally continued by the conversion of the product of formula (1) in which R2 is O-M +, where M + is a metal such as Na, Li or K, in a compound of formula (1) in which R2 is OH, by treatment with a source of protons, which can optionally be converted into a compound of formula (1 ) wherein R2 is O-M + (where M + is a protonated amine moiety as defined previously), by treatment with a corresponding amine, optionally followed, if a compound of formula (2) or (3), of the asymmetric reduction of a compound of formula (1) to provide a compound of formula (2) or (3). |
| priorityDate | 2000-10-16-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
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Total number of triples: 58.