FR2639943A1 - Catalyseur et procede de synthese asymetrique de la cyanhydrine du m-phenoxybenzaldehyde - Google Patents
Catalyseur et procede de synthese asymetrique de la cyanhydrine du m-phenoxybenzaldehyde Download PDFInfo
- Publication number
- FR2639943A1 FR2639943A1 FR8915992A FR8915992A FR2639943A1 FR 2639943 A1 FR2639943 A1 FR 2639943A1 FR 8915992 A FR8915992 A FR 8915992A FR 8915992 A FR8915992 A FR 8915992A FR 2639943 A1 FR2639943 A1 FR 2639943A1
- Authority
- FR
- France
- Prior art keywords
- catalyst
- xad
- histidine
- cyclo
- cph
- Prior art date
- 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.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 54
- 238000000034 method Methods 0.000 title claims abstract description 19
- MRLGCTNJRREZHZ-UHFFFAOYSA-N 3-phenoxybenzaldehyde Chemical compound O=CC1=CC=CC(OC=2C=CC=CC=2)=C1 MRLGCTNJRREZHZ-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000011914 asymmetric synthesis Methods 0.000 title claims description 8
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-UHFFFAOYSA-N 0.000 title claims description 3
- 239000007787 solid Substances 0.000 claims abstract description 15
- 230000008569 process Effects 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 11
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 8
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 8
- OHUXOEXBXPZKPT-STQMWFEESA-N Phe-His Chemical class C([C@H](N)C(=O)N[C@@H](CC=1N=CNC=1)C(O)=O)C1=CC=CC=C1 OHUXOEXBXPZKPT-STQMWFEESA-N 0.000 claims abstract description 7
- 239000002952 polymeric resin Substances 0.000 claims abstract description 5
- 229920003002 synthetic resin Polymers 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 44
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 229920005989 resin Polymers 0.000 claims description 14
- 239000011347 resin Substances 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 238000004064 recycling Methods 0.000 claims description 6
- 108010092114 histidylphenylalanine Proteins 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 229920001577 copolymer Polymers 0.000 claims description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 claims 1
- 150000002410 histidine derivatives Chemical class 0.000 claims 1
- 229920000831 ionic polymer Polymers 0.000 claims 1
- 125000000405 phenylalanyl group Chemical group 0.000 claims 1
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920001429 chelating resin Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000003463 adsorbent Substances 0.000 description 4
- 108010016626 Dipeptides Proteins 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 229920002223 polystyrene Polymers 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 108010069514 Cyclic Peptides Proteins 0.000 description 1
- 102000001189 Cyclic Peptides Human genes 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 208000003870 Drug Overdose Diseases 0.000 description 1
- 206010033296 Overdoses Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000796486 Tetilla arb Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007883 cyanide addition reaction Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 231100000725 drug overdose Toxicity 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 239000002052 molecular layer Substances 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0237—Amines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/36—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL88618A IL88618A (en) | 1988-12-07 | 1988-12-07 | Chiral cyanohydrination of m-phenoxybenzaldehyde over polymer-supported cyclo (phenylalanyl- histidine) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2639943A1 true FR2639943A1 (fr) | 1990-06-08 |
| FR2639943B1 FR2639943B1 (enExample) | 1993-02-26 |
Family
ID=11059474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8915992A Granted FR2639943A1 (fr) | 1988-12-07 | 1989-12-04 | Catalyseur et procede de synthese asymetrique de la cyanhydrine du m-phenoxybenzaldehyde |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5057477A (enExample) |
| JP (1) | JPH02265650A (enExample) |
| FR (1) | FR2639943A1 (enExample) |
| GB (1) | GB2227429B (enExample) |
| HU (1) | HU207000B (enExample) |
| IL (1) | IL88618A (enExample) |
| NL (1) | NL8902982A (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2302552A1 (en) * | 1997-09-08 | 1999-03-18 | Chugai Seiyaku Kabushiki Kaisha | Process for selectively oxidizing primary hydroxyl groups of organic compounds, and resin containing adsorbed catalyst for use therein |
| US7556695B2 (en) * | 2002-05-06 | 2009-07-07 | Honeywell International, Inc. | Apparatus to make nanolaminate thermal barrier coatings |
| DK1439220T3 (da) * | 2003-01-16 | 2007-12-27 | Adorkem Technology Spa | Immobiliserede biokatalysatorer der kan anvendes til fremstilling af naturlige nukleosider og modificerede analoger ved enzymatiske transglycosyleringsreaktioner |
| ES2717135T3 (es) | 2005-07-20 | 2019-06-19 | Ascensia Diabetes Care Holdings Ag | Método para señalar al usuario para que añada una muestra adicional a una tira de prueba, método para medir la temperatura de una muestra y métodos para determinar la concentración de un analito basados en amperometría controlada |
| KR20130100022A (ko) | 2005-09-30 | 2013-09-06 | 바이엘 헬스케어 엘엘씨 | 게이트형 전압 전류 측정 분석물 결정 방법 |
| JP5244116B2 (ja) * | 2006-10-24 | 2013-07-24 | バイエル・ヘルスケア・エルエルシー | 過渡減衰電流測定法 |
| WO2009076302A1 (en) | 2007-12-10 | 2009-06-18 | Bayer Healthcare Llc | Control markers for auto-detection of control solution and methods of use |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0135691A2 (en) * | 1983-09-26 | 1985-04-03 | E.I. Du Pont De Nemours And Company | Cyanohydrination catalyst |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU576322B2 (en) * | 1983-07-22 | 1988-08-25 | Ici Australia Limited | Alpha-substituted-alpha-cyanomethyl alcohols |
| US4569793A (en) * | 1984-09-26 | 1986-02-11 | Shell Oil Company | Cyanohydrination catalyst |
| US4611076A (en) * | 1985-06-26 | 1986-09-09 | Shell Oil Company | Chiral cyanohydrination process |
| FR2600208B1 (fr) * | 1986-06-12 | 1992-07-03 | Peugeot | Contacteur pour organe de commande actionne au pied et son application a une pedale de frein, notamment d'automobile |
-
1988
- 1988-12-07 IL IL88618A patent/IL88618A/xx not_active IP Right Cessation
-
1989
- 1989-12-04 FR FR8915992A patent/FR2639943A1/fr active Granted
- 1989-12-04 NL NL8902982A patent/NL8902982A/nl not_active Application Discontinuation
- 1989-12-05 GB GB8927501A patent/GB2227429B/en not_active Expired - Lifetime
- 1989-12-06 JP JP1315494A patent/JPH02265650A/ja active Pending
- 1989-12-06 US US07/447,095 patent/US5057477A/en not_active Expired - Fee Related
- 1989-12-06 HU HU896447A patent/HU207000B/hu not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0135691A2 (en) * | 1983-09-26 | 1985-04-03 | E.I. Du Pont De Nemours And Company | Cyanohydrination catalyst |
Non-Patent Citations (1)
| Title |
|---|
| BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN. vol. 59, no. 3, Mars 1986, TOKYO JP pages 893 - 895; YOSHIYUKI KOBAYASHI ET AL.: 'Asymmmetric Addition of Hydrogen Cyanide to Substituted Benzaldehydes Catalyzed by a Synthetic Cyclic Peptide, Cyclo((S)-phenylalanyl-(S)-histidyl)' * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8927501D0 (en) | 1990-02-07 |
| GB2227429B (en) | 1992-08-05 |
| US5057477A (en) | 1991-10-15 |
| HU207000B (en) | 1993-03-01 |
| GB2227429A (en) | 1990-08-01 |
| FR2639943B1 (enExample) | 1993-02-26 |
| JPH02265650A (ja) | 1990-10-30 |
| IL88618A (en) | 1993-02-21 |
| HUT52713A (en) | 1990-08-28 |
| IL88618A0 (en) | 1989-07-31 |
| HU896447D0 (en) | 1990-02-28 |
| NL8902982A (nl) | 1990-07-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |