CA2523096A1 - Procede de preparation de l'acide 3,4-dihydroxybutanoique - Google Patents

Procede de preparation de l'acide 3,4-dihydroxybutanoique Download PDF

Info

Publication number: CA2523096A1
Authority: CA; Canada
Prior art keywords: reaction mixture; acid; hexose; base; source
Prior art date: 2000-04-24
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Abandoned

Application number

CA002523096A

Other languages

English (en)

Inventor

Rawle I. Hollingsworth

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Michigan State University MSU

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-04-24

Filing date

2001-03-05

Publication date

2001-11-01

2000-04-24 Priority claimed from US09/556,532 external-priority patent/US6239311B1/en

2001-03-05 Application filed by Individual filed Critical Individual

2001-11-01 Publication of CA2523096A1 publication Critical patent/CA2523096A1/fr

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 74
230000008569 process Effects 0.000 title claims abstract description 69
DZAIOXUZHHTJKN-UHFFFAOYSA-N 3,4-dihydroxybutyric acid Chemical compound OCC(O)CC(O)=O DZAIOXUZHHTJKN-UHFFFAOYSA-N 0.000 title claims abstract description 44
238000002360 preparation method Methods 0.000 title abstract description 11
239000011541 reaction mixture Substances 0.000 claims abstract description 64
239000002585 base Substances 0.000 claims abstract description 47
150000002978 peroxides Chemical class 0.000 claims abstract description 40
239000007800 oxidant agent Substances 0.000 claims abstract description 32
150000003839 salts Chemical class 0.000 claims abstract description 29
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims abstract description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 54
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 48
238000006243 chemical reaction Methods 0.000 claims description 33
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 32
239000000047 product Substances 0.000 claims description 32
-1 cyclic ester Chemical class 0.000 claims description 25
239000000203 mixture Substances 0.000 claims description 19
239000008103 glucose Substances 0.000 claims description 16
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 15
238000010438 heat treatment Methods 0.000 claims description 15
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 14
150000002402 hexoses Chemical class 0.000 claims description 12
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 11
229920002472 Starch Polymers 0.000 claims description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
235000019698 starch Nutrition 0.000 claims description 10
239000008107 starch Substances 0.000 claims description 10
229920002774 Maltodextrin Polymers 0.000 claims description 9
OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims description 8
GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims description 8
235000000346 sugar Nutrition 0.000 claims description 8
WQZGKKKJIJFFOK-ZZWDRFIYSA-N L-glucose Chemical compound OC[C@@H]1OC(O)[C@@H](O)[C@H](O)[C@H]1O WQZGKKKJIJFFOK-ZZWDRFIYSA-N 0.000 claims description 7
GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 claims description 7
238000004821 distillation Methods 0.000 claims description 7
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 6
229920002678 cellulose Polymers 0.000 claims description 6
239000001913 cellulose Substances 0.000 claims description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
235000019253 formic acid Nutrition 0.000 claims description 5
125000000457 gamma-lactone group Chemical group 0.000 claims description 5
239000008101 lactose Substances 0.000 claims description 5
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 4
239000005913 Maltodextrin Substances 0.000 claims description 4
VIHAEDVKXSOUAT-UHFFFAOYSA-N but-2-en-4-olide Chemical compound O=C1OCC=C1 VIHAEDVKXSOUAT-UHFFFAOYSA-N 0.000 claims description 4
150000002148 esters Chemical class 0.000 claims description 4
229940035034 maltodextrin Drugs 0.000 claims description 4
GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 claims description 3
150000004974 alkaline earth metal peroxides Chemical class 0.000 claims description 3
230000006872 improvement Effects 0.000 claims description 3
150000004973 alkali metal peroxides Chemical class 0.000 claims description 2
WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 2
229920001542 oligosaccharide Polymers 0.000 claims description 2
DZAIOXUZHHTJKN-VKHMYHEASA-N 3S,4-dihydroxy-butyric acid Chemical compound OC[C@@H](O)CC(O)=O DZAIOXUZHHTJKN-VKHMYHEASA-N 0.000 claims 3
125000000686 lactone group Chemical group 0.000 claims 2
125000004122 cyclic group Chemical group 0.000 claims 1
239000000413 hydrolysate Substances 0.000 claims 1
159000000000 sodium salts Chemical class 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 10
FUDDLSHBRSNCBV-UHFFFAOYSA-N 4-hydroxyoxolan-2-one Chemical compound OC1COC(=O)C1 FUDDLSHBRSNCBV-UHFFFAOYSA-N 0.000 abstract description 3
150000001340 alkali metals Chemical class 0.000 abstract description 3
230000020477 pH reduction Effects 0.000 abstract description 3
239000000126 substance Substances 0.000 abstract description 3
RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 abstract description 2
235000014113 dietary fatty acids Nutrition 0.000 abstract description 2
229930195729 fatty acid Natural products 0.000 abstract description 2
239000000194 fatty acid Substances 0.000 abstract description 2
229910000272 alkali metal oxide Inorganic materials 0.000 abstract 1
150000004665 fatty acids Chemical class 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 35
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
150000002596 lactones Chemical class 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 21
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
238000000605 extraction Methods 0.000 description 11
DLVZBSZXZDGKQY-UHFFFAOYSA-N 2,2-dihydroxybutanoic acid Chemical compound CCC(O)(O)C(O)=O DLVZBSZXZDGKQY-UHFFFAOYSA-N 0.000 description 10
238000005481 NMR spectroscopy Methods 0.000 description 10
150000001720 carbohydrates Chemical class 0.000 description 10
230000003647 oxidation Effects 0.000 description 10
238000007254 oxidation reaction Methods 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
235000014633 carbohydrates Nutrition 0.000 description 9
239000006188 syrup Substances 0.000 description 9
235000020357 syrup Nutrition 0.000 description 9
238000002955 isolation Methods 0.000 description 8
239000000463 material Substances 0.000 description 8
239000000243 solution Substances 0.000 description 8
150000001412 amines Chemical class 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
238000007363 ring formation reaction Methods 0.000 description 7
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
NKNFUMKGJYKPCT-UHFFFAOYSA-N n,n-diethylethanamine;sulfuric acid Chemical compound [O-]S([O-])(=O)=O.CC[NH+](CC)CC.CC[NH+](CC)CC NKNFUMKGJYKPCT-UHFFFAOYSA-N 0.000 description 6
229910001415 sodium ion Inorganic materials 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 5
239000006227 byproduct Substances 0.000 description 5
239000000543 intermediate Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
230000009466 transformation Effects 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 4
239000003814 drug Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
230000015556 catabolic process Effects 0.000 description 3
238000006731 degradation reaction Methods 0.000 description 3
230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
150000001261 hydroxy acids Chemical class 0.000 description 3
239000012535 impurity Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000758 substrate Substances 0.000 description 3
238000000844 transformation Methods 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229920000858 Cyclodextrin Polymers 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000003513 alkali Substances 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
238000013459 approach Methods 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
235000012000 cholesterol Nutrition 0.000 description 2
238000011161 development Methods 0.000 description 2
125000005594 diketone group Chemical group 0.000 description 2
239000012634 fragment Substances 0.000 description 2
238000004817 gas chromatography Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
238000005342 ion exchange Methods 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical group O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 2
150000008163 sugars Chemical class 0.000 description 2
QXJDESBAUIILLG-UHFFFAOYSA-N 1,2,3,3,4,4,4-heptafluoro-1-iodobut-1-ene Chemical compound FC(I)=C(F)C(F)(F)C(F)(F)F QXJDESBAUIILLG-UHFFFAOYSA-N 0.000 description 1
UFYGCFHQAXXBCF-UHFFFAOYSA-N 2,4-dihydroxybutanoic acid Chemical compound OCCC(O)C(O)=O UFYGCFHQAXXBCF-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
BEMNKPXNGWTBLQ-OXIQGZBJSA-N Aplysistatin Natural products CC1(C)[C@@H](Br)CC[C@]2(C)O[C@H]3COC(=O)C3=CC[C@H]12 BEMNKPXNGWTBLQ-OXIQGZBJSA-N 0.000 description 1
XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 1
208000023514 Barrett esophagus Diseases 0.000 description 1
VWFCHDSQECPREK-LURJTMIESA-N Cidofovir Chemical compound NC=1C=CN(C[C@@H](CO)OCP(O)(O)=O)C(=O)N=1 VWFCHDSQECPREK-LURJTMIESA-N 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
QXKAIJAYHKCRRA-JJYYJPOSSA-N D-arabinonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(O)=O QXKAIJAYHKCRRA-JJYYJPOSSA-N 0.000 description 1
JPIJQSOTBSSVTP-PWNYCUMCSA-N D-erythronic acid Chemical compound OC[C@@H](O)[C@@H](O)C(O)=O JPIJQSOTBSSVTP-PWNYCUMCSA-N 0.000 description 1
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 1
DGVNSEIPAGRXCN-PTLFGRINSA-N O[C@H]1CC(=O)OC1O Chemical compound O[C@H]1CC(=O)OC1O DGVNSEIPAGRXCN-PTLFGRINSA-N 0.000 description 1
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235000011941 Tilia x europaea Nutrition 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
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150000001342 alkaline earth metals Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
238000005349 anion exchange Methods 0.000 description 1
238000005571 anion exchange chromatography Methods 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000000840 anti-viral effect Effects 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
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239000007864 aqueous solution Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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244000309464 bull Species 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
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238000011067 equilibration Methods 0.000 description 1
AIZRKZQHJNWBEI-YFKPBYRVSA-N ethyl (3s)-4-bromo-3-hydroxybutanoate Chemical compound CCOC(=O)C[C@H](O)CBr AIZRKZQHJNWBEI-YFKPBYRVSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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RBNPOMFGQQGHHO-UHFFFAOYSA-N glyceric acid Chemical class OCC(O)C(O)=O RBNPOMFGQQGHHO-UHFFFAOYSA-N 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
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PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
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238000007726 management method Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
HOVAGTYPODGVJG-UHFFFAOYSA-N methyl beta-galactoside Natural products COC1OC(CO)C(O)C(O)C1O HOVAGTYPODGVJG-UHFFFAOYSA-N 0.000 description 1
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238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
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239000003348 petrochemical agent Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
150000003077 polyols Chemical group 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
PTMFUWGXPRYYMC-UHFFFAOYSA-N triethylazanium;formate Chemical compound OC=O.CCN(CC)CC PTMFUWGXPRYYMC-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
229910021511 zinc hydroxide Inorganic materials 0.000 description 1
229940007718 zinc hydroxide Drugs 0.000 description 1
150000003952 β-lactams Chemical class 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA002523096A 2000-04-24 2001-03-05 Procede de preparation de l'acide 3,4-dihydroxybutanoique Abandoned CA2523096A1 (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US09/556,532		2000-04-24
US09/556,532 US6239311B1 (en)	2000-04-24	2000-04-24	Process for the preparation of 3,4-dihydroxybutanoic acid and salts and lactones derived therefrom
CA002373927A CA2373927C (fr)	2000-04-24	2001-03-05	Procede ameliore de preparation d'acide 3,4-dihydroxybutanoique et de sels et de lactones derives dudit acide

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002373927A Division CA2373927C (fr)	2000-04-24	2001-03-05	Procede ameliore de preparation d'acide 3,4-dihydroxybutanoique et de sels et de lactones derives dudit acide

Publications (1)

Publication Number	Publication Date
CA2523096A1 true CA2523096A1 (fr)	2001-11-01

Family

ID=35478585

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002523096A Abandoned CA2523096A1 (fr)	2000-04-24	2001-03-05	Procede de preparation de l'acide 3,4-dihydroxybutanoique

Country Status (1)

Country	Link
CA (1)	CA2523096A1 (fr)

2001
- 2001-03-05 CA CA002523096A patent/CA2523096A1/fr not_active Abandoned

Legal Events

Date	Code	Title	Description
2005-11-01	EEER	Examination request
2010-11-15	FZDE	Dead

Publication	Publication Date	Title
EP0513430B1 (fr)	1995-01-25	Procédé pour la préparation de l'acide 3,4-dihydroxybutanoique et ses sels
CA2304809C (fr)	2006-08-01	Procede de preparation de gamma butyrolactones a substitution hydroxy
US5563303A (en)	1996-10-08	Production of xylitol
WO2000034221A1 (fr)	2000-06-15	Elimination de l'acide nitrique de produits d'oxydation
JP2016512826A (ja)	2016-05-09	ケトカルボン酸を含む組成物からのジカルボン酸および誘導体の製造方法
DE69903441T2 (de)	2003-08-14	VERFAHREN ZUR BEREITUNG VON OPTISCH REINEM ( DOLLAR i (S))-3-HYDROXY-GAMMA-BUTYROLACTON
CA2373927C (fr)	2007-05-29	Procede ameliore de preparation d'acide 3,4-dihydroxybutanoique et de sels et de lactones derives dudit acide
US20090112002A1 (en)	2009-04-30	Process for preparation of aldonic acids and derivatives thereof
US6713639B1 (en)	2004-03-30	Process for preparing enantiomerically pure (S)-3-hydroxy-gamma-butyrolactone
CA2523096A1 (fr)	2001-11-01	Procede de preparation de l'acide 3,4-dihydroxybutanoique
JP7194947B2 (ja)	2022-12-23	シクロペンテノン誘導体の製造方法
US6288244B1 (en)	2001-09-11	Process for the preparation of 3, 4-dihydroxybutanoic acid and derivatives thereof from substituted pentose sugars
Gamalevich et al.	1999	Lipase-mediated ‘meso-tricks’ to transform latently symmetrical d-aldoses into l-aldoses via alditols
RU2455296C2 (ru)	2012-07-10	Способ получения альдоновых кислот и их производных