DK2089351T3 - Stereoselektiv ettrins-fluoreringsfremgangsmåde til fremstilling af 2-fluorpropionat - Google Patents
Stereoselektiv ettrins-fluoreringsfremgangsmåde til fremstilling af 2-fluorpropionat Download PDFInfo
- Publication number
- DK2089351T3 DK2089351T3 DK07819014.7T DK07819014T DK2089351T3 DK 2089351 T3 DK2089351 T3 DK 2089351T3 DK 07819014 T DK07819014 T DK 07819014T DK 2089351 T3 DK2089351 T3 DK 2089351T3
- Authority
- DK
- Denmark
- Prior art keywords
- formula
- carbon atom
- process according
- methyl
- lactic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- ZVZPFTCEXIGSHM-UHFFFAOYSA-N 2-fluoropropanoic acid Chemical compound CC(F)C(O)=O ZVZPFTCEXIGSHM-UHFFFAOYSA-N 0.000 title description 4
- 230000000707 stereoselective effect Effects 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims description 9
- -1 tetrafluoroethyl dimethylamine Chemical compound 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 11
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 239000011737 fluorine Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000003682 fluorination reaction Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- VIRGYRZBWQFJGJ-UHFFFAOYSA-N 1,1,2,2-tetrafluoro-n,n-dimethylethanamine Chemical compound CN(C)C(F)(F)C(F)F VIRGYRZBWQFJGJ-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000003903 lactic acid esters Chemical class 0.000 description 4
- BNTFCVMJHBNJAR-UHFFFAOYSA-N n,n-diethyl-1,1,2,3,3,3-hexafluoropropan-1-amine Chemical compound CCN(CC)C(F)(F)C(F)C(F)(F)F BNTFCVMJHBNJAR-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- MHAIQPNJLRLFLO-GSVOUGTGSA-N methyl (2r)-2-fluoropropanoate Chemical compound COC(=O)[C@@H](C)F MHAIQPNJLRLFLO-GSVOUGTGSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 2
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- HPKZHKRTMMLVBQ-UHFFFAOYSA-N fluoro propanoate Chemical compound CCC(=O)OF HPKZHKRTMMLVBQ-UHFFFAOYSA-N 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- IUEWOPMXNADAEB-UHFFFAOYSA-N 2,2-difluoro-n,n-dimethylacetamide Chemical compound CN(C)C(=O)C(F)F IUEWOPMXNADAEB-UHFFFAOYSA-N 0.000 description 1
- APOYTRAZFJURPB-UHFFFAOYSA-N 2-methoxy-n-(2-methoxyethyl)-n-(trifluoro-$l^{4}-sulfanyl)ethanamine Chemical compound COCCN(S(F)(F)F)CCOC APOYTRAZFJURPB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- LZCLXQDLBQLTDK-BYPYZUCNSA-N ethyl (2S)-lactate Chemical compound CCOC(=O)[C@H](C)O LZCLXQDLBQLTDK-BYPYZUCNSA-N 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-VKHMYHEASA-N methyl (S)-lactate Chemical compound COC(=O)[C@H](C)O LPEKGGXMPWTOCB-VKHMYHEASA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- SLVAEVYIJHDKRO-UHFFFAOYSA-N trifluoromethanesulfonyl fluoride Chemical compound FC(F)(F)S(F)(=O)=O SLVAEVYIJHDKRO-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/307—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by introduction of halogen; by substitution of halogen atoms by other halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (4)
1. Fremgangsmåde til fremstilling af en forbindelse med formel (II)
(II) hvor ** markerer et asymmetrisk carbonatom, R1 er eventuelt substitueret Ci-C4~alkyl, og R2 er eventuelt substitueret methyl, der er kendetegnet ved, at tetrafluorethyldimethylamin reageres med et mælkesyrederivat med formel (I)
(i) hvor * markerer et asymmetrisk carbonatom i R- eller S-konfiguration, og R1 og R2 har betydningen, der er anført ovenfor, carbonatomet markeret med ** i formel (II) har omvendt konfiguration sammenlignet med det tilsvarende carbonatom markeret med * i formel (I), og hvor reaktionen udføres under nedkøling og dråbevis blanding af begge edukter ved temperaturer på mellem 0 °C og 30 °C.
2. Fremgangsmåde ifølge krav 1, der er kendetegnet ved, at reaktionen finder sted i nærvær af et inert fortyndingsmiddel.
3. Fremgangsmåde ifølge krav 1 eller 2, der er kendetegnet ved, at mellem 0,75 og 3 mol af tetraf luorethyldimethylamin reageres pr. mol mælkesyrederivat med formel (I).
4. Fremgangsmåde ifølge et hvilket som helst af kravene 1 til 3, der er kendetegnet ved, at R1 og R2 begge er methyl.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06022482 | 2006-10-27 | ||
| PCT/EP2007/008944 WO2008049531A1 (en) | 2006-10-27 | 2007-10-16 | Stereoselective one step fluorination process for the preparation of 2-fluoropropionate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2089351T3 true DK2089351T3 (da) | 2017-04-24 |
Family
ID=38904625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK07819014.7T DK2089351T3 (da) | 2006-10-27 | 2007-10-16 | Stereoselektiv ettrins-fluoreringsfremgangsmåde til fremstilling af 2-fluorpropionat |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8093421B2 (da) |
| EP (1) | EP2089351B1 (da) |
| JP (1) | JP5514549B2 (da) |
| KR (1) | KR101406436B1 (da) |
| CN (1) | CN101528662B (da) |
| BR (1) | BRPI0718190B1 (da) |
| DK (1) | DK2089351T3 (da) |
| ES (1) | ES2622414T3 (da) |
| IL (1) | IL198302A (da) |
| TW (1) | TWI411603B (da) |
| WO (1) | WO2008049531A1 (da) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5775078B2 (ja) | 2009-08-21 | 2015-09-09 | スリーエム イノベイティブ プロパティズ カンパニー | 耐水性応力分散材料を用いる、組織損傷を低減するための方法及び製品 |
| CN105037150B (zh) * | 2015-07-22 | 2017-11-21 | 巨化集团技术中心 | 一种2‑氟丙酸酯的合成方法 |
| CN109627165B (zh) * | 2018-10-31 | 2022-06-21 | 浙江巨化技术中心有限公司 | 一种联产2-氟丙酸酯和二氟乙酸乙酯的方法 |
| CA3153003C (en) | 2018-11-29 | 2023-10-17 | Bayer Cropscience Lp | Herbicidal compositions for animal grazelands and methods for applying the same |
| JP7652598B2 (ja) | 2021-03-22 | 2025-03-27 | 国立大学法人 名古屋工業大学 | ２－フルオロメチルアクリル酸エステル誘導体の製造方法 |
| CN118515558B (zh) * | 2024-04-25 | 2026-02-17 | 福建永晶科技股份有限公司 | 一种用二乙胺基三氟化硫制备具有光学活性的氟代丙酸甲酯的方法 |
| CN120117983A (zh) * | 2025-05-13 | 2025-06-10 | 山东国邦药业有限公司 | 一种制备具有光学活性2-(r)-氟丙酸甲酯的方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19522703A1 (de) * | 1995-06-22 | 1997-01-02 | Bayer Ag | Verfahren zur Herstellung von 2-Fluor-isobuttersäurealkylestern |
| WO2006018991A1 (ja) | 2004-08-18 | 2006-02-23 | Central Glass Company, Limited | 光学活性α－フルオロカルボン酸エステル誘導体の製造方法 |
| JP4839724B2 (ja) * | 2004-08-18 | 2011-12-21 | セントラル硝子株式会社 | 光学活性α−フルオロカルボン酸エステル誘導体の製造方法 |
| DE102004060493A1 (de) * | 2004-12-16 | 2006-07-06 | Lanxess Deutschland Gmbh | Verfahren zur Herstellung von enantiomerenangereicherten 2-Fluorcarbonsäureestern |
| JP5186722B2 (ja) * | 2005-03-18 | 2013-04-24 | セントラル硝子株式会社 | スルフリルフルオリドを用いるフッ素化反応 |
| JP4940790B2 (ja) * | 2006-06-30 | 2012-05-30 | セントラル硝子株式会社 | 脱ヒドロキシフッ素化剤 |
| JP5109530B2 (ja) * | 2007-01-23 | 2012-12-26 | セントラル硝子株式会社 | 光学活性α−フルオロカルボン酸エステルの製造方法 |
| DE102007005296A1 (de) * | 2007-02-02 | 2008-08-07 | Bayer Cropscience Ag | Verfahren zum Herstellen von Dihaloacetessigsäurealkylestern |
-
2007
- 2007-10-16 DK DK07819014.7T patent/DK2089351T3/da active
- 2007-10-16 KR KR1020097010731A patent/KR101406436B1/ko active Active
- 2007-10-16 WO PCT/EP2007/008944 patent/WO2008049531A1/en not_active Ceased
- 2007-10-16 ES ES07819014.7T patent/ES2622414T3/es active Active
- 2007-10-16 US US12/446,774 patent/US8093421B2/en active Active
- 2007-10-16 BR BRPI0718190A patent/BRPI0718190B1/pt active IP Right Grant
- 2007-10-16 CN CN2007800398977A patent/CN101528662B/zh active Active
- 2007-10-16 JP JP2009533697A patent/JP5514549B2/ja active Active
- 2007-10-16 EP EP07819014.7A patent/EP2089351B1/en active Active
- 2007-10-26 TW TW096140167A patent/TWI411603B/zh active
-
2009
- 2009-04-22 IL IL198302A patent/IL198302A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| TWI411603B (zh) | 2013-10-11 |
| KR101406436B1 (ko) | 2014-06-13 |
| US8093421B2 (en) | 2012-01-10 |
| CN101528662A (zh) | 2009-09-09 |
| KR20090080101A (ko) | 2009-07-23 |
| IL198302A (en) | 2012-08-30 |
| EP2089351B1 (en) | 2017-01-25 |
| ES2622414T3 (es) | 2017-07-06 |
| JP5514549B2 (ja) | 2014-06-04 |
| CN101528662B (zh) | 2013-04-17 |
| WO2008049531A1 (en) | 2008-05-02 |
| IL198302A0 (en) | 2010-02-17 |
| EP2089351A1 (en) | 2009-08-19 |
| US20100069663A1 (en) | 2010-03-18 |
| TW200833659A (en) | 2008-08-16 |
| JP2010507604A (ja) | 2010-03-11 |
| BRPI0718190B1 (pt) | 2017-03-07 |
| BRPI0718190A2 (pt) | 2013-11-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DK2089351T3 (da) | Stereoselektiv ettrins-fluoreringsfremgangsmåde til fremstilling af 2-fluorpropionat | |
| US20110213176A1 (en) | Process for Producing alpha Substituted Ester | |
| US8304576B2 (en) | Process for production of halogenated alpha-fluoroethers | |
| US9440917B2 (en) | Method for producing 4-haloalkyl-3-mercapto-substituted 2-hydroxy-benzoic acid derivatives | |
| JP2024544694A (ja) | イソオキサゾリンカルボン酸誘導体を生成する方法 | |
| JP5001144B2 (ja) | ２−イソプロペニル−５−メチル−４−ヘキセン−１−イル３−メチル−２−ブテノアートの製造方法 | |
| JP5186115B2 (ja) | ２‐置換ベンジル‐３，３‐ジフルオロアクリル酸エステル誘導体及びそれらの製造方法 | |
| JP4968066B2 (ja) | ４−アミノ−２−アルキルチオ−５−ピリミジンカルバルデヒドの製法 | |
| JP4608888B2 (ja) | ２−シアノ−２−（４−テトラヒドロピラニル）酢酸エステルの製法 | |
| KR20140107364A (ko) | 2,6-다이플루오로아세토페논의 제조 방법 | |
| WO2013038931A1 (ja) | 2-オキソ-2H-シクロヘプタ[b]フラン類縁体の製造方法 | |
| JP5378688B2 (ja) | フッ素化試薬組成物およびｇｅｍ−ジフルオロ化合物の製造方法 | |
| US20040176644A1 (en) | Process for producing 2-phenylacetophenone derivatives and precursons therefor | |
| JP2009269870A (ja) | ３−ヒドロキシアクリロニトリルの金属塩の製造方法 | |
| JP2008247835A (ja) | メトキシ基を有するβ−ジケトン化合物の製法 | |
| JP2008007415A (ja) | 新規な含フッ素不飽和シリルエーテル化合物及び該化合物を中間体とする含フッ素不飽和アルコール誘導体の製造方法 | |
| JP2002201169A (ja) | ４−シアノ−３−オキソブタン酸エステルの製造法 | |
| JPH10130204A (ja) | ４−ハロゲノ−３−トリフルオロメチルフェノキシブタン酸エステル類の製造法 | |
| JP2008120759A (ja) | エーテル基を有するβ−ジケトン化合物の製造法 | |
| JP2009013119A (ja) | プロパン化合物の製造方法 | |
| JP2002249476A (ja) | 光学活性３−置換−２−シアノブタンジカルボン酸類の製造方法 | |
| JP2009013118A (ja) | アルカン化合物の製造方法 | |
| JP2008266183A (ja) | ３，４−ジアルコキシ−２−（アルキルチオ）フェノールの製法 |