JPH0440660B2 - - Google Patents
Info
- Publication number
- JPH0440660B2 JPH0440660B2 JP57131378A JP13137882A JPH0440660B2 JP H0440660 B2 JPH0440660 B2 JP H0440660B2 JP 57131378 A JP57131378 A JP 57131378A JP 13137882 A JP13137882 A JP 13137882A JP H0440660 B2 JPH0440660 B2 JP H0440660B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- optically active
- packing material
- general formula
- chromatographic packing
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- -1 3-(2-methyl-1 -propenyl)-2,2-dimethyl-1-cyclopropyl group Chemical group 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 15
- 238000012856 packing Methods 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
- 239000000741 silica gel Substances 0.000 claims description 14
- 229910002027 silica gel Inorganic materials 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 10
- 150000001282 organosilanes Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 238000004811 liquid chromatography Methods 0.000 claims description 6
- 238000004458 analytical method Methods 0.000 claims description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
- 239000000945 filler Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 9
- 238000000926 separation method Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- VTJMSIIXXKNIDJ-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutyric acid Chemical group CC(C)C(C(O)=O)C1=CC=C(Cl)C=C1 VTJMSIIXXKNIDJ-UHFFFAOYSA-N 0.000 description 5
- 150000005331 phenylglycines Chemical class 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000723353 Chrysanthemum Species 0.000 description 4
- 235000007516 Chrysanthemum Nutrition 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229940024606 amino acid Drugs 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- 230000005526 G1 to G0 transition Effects 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- YNWVFADWVLCOPU-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1C(C(O)C(C)(C)C)=CC1=CC=C(Cl)C=C1 YNWVFADWVLCOPU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical compound C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- BWPYAVCZZUTOBY-UHFFFAOYSA-N 2-(4-chlorophenyl)-3-methylbutanoyl chloride Chemical compound CC(C)C(C(Cl)=O)C1=CC=C(Cl)C=C1 BWPYAVCZZUTOBY-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- GCIARMDXQWNVJF-UHFFFAOYSA-N 3-trichlorosilylpropan-1-amine Chemical compound NCCC[Si](Cl)(Cl)Cl GCIARMDXQWNVJF-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- 108010016626 Dipeptides Proteins 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 229940051881 anilide analgesics and antipyretics Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 229960004295 valine Drugs 0.000 description 1
- 238000005406 washing Methods 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J20/286—Phases chemically bonded to a substrate, e.g. to silica or to polymers
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/281—Sorbents specially adapted for preparative, analytical or investigative chromatography
- B01J20/29—Chiral phases
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3202—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the carrier, support or substrate used for impregnation or coating
- B01J20/3204—Inorganic carriers, supports or substrates
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3214—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the method for obtaining this coating or impregnating
- B01J20/3217—Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond
- B01J20/3219—Resulting in a chemical bond between the coating or impregnating layer and the carrier, support or substrate, e.g. a covalent bond involving a particular spacer or linking group, e.g. for attaching an active group
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
- B01J20/3244—Non-macromolecular compounds
- B01J20/3246—Non-macromolecular compounds having a well defined chemical structure
- B01J20/3257—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one of the heteroatoms nitrogen, oxygen or sulfur together with at least one silicon atom, these atoms not being part of the carrier as such
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
- B01J20/3244—Non-macromolecular compounds
- B01J20/3246—Non-macromolecular compounds having a well defined chemical structure
- B01J20/3257—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one of the heteroatoms nitrogen, oxygen or sulfur together with at least one silicon atom, these atoms not being part of the carrier as such
- B01J20/3259—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one of the heteroatoms nitrogen, oxygen or sulfur together with at least one silicon atom, these atoms not being part of the carrier as such comprising at least two different types of heteroatoms selected from nitrogen, oxygen or sulfur with at least one silicon atom
-
- 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
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/32—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating
- B01J20/3231—Impregnating or coating ; Solid sorbent compositions obtained from processes involving impregnating or coating characterised by the coating or impregnating layer
- B01J20/3242—Layers with a functional group, e.g. an affinity material, a ligand, a reactant or a complexing group
- B01J20/3244—Non-macromolecular compounds
- B01J20/3246—Non-macromolecular compounds having a well defined chemical structure
- B01J20/3257—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one of the heteroatoms nitrogen, oxygen or sulfur together with at least one silicon atom, these atoms not being part of the carrier as such
- B01J20/3261—Non-macromolecular compounds having a well defined chemical structure the functional group or the linking, spacer or anchoring group as a whole comprising at least one of the heteroatoms nitrogen, oxygen or sulfur together with at least one silicon atom, these atoms not being part of the carrier as such comprising a cyclic structure not containing any of the heteroatoms nitrogen, oxygen or sulfur, e.g. aromatic structures
-
- 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
- B01J2220/00—Aspects relating to sorbent materials
- B01J2220/50—Aspects relating to the use of sorbent or filter aid materials
- B01J2220/54—Sorbents specially adapted for analytical or investigative chromatography
Landscapes
- Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
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ãè¡šãDETAILED DESCRIPTION OF THE INVENTION The present invention provides a chromatographic packing material grafted with a novel optically active organosilane, and an -NH- group, -OCNH- group,
There is a method for separating and analyzing an enantiomeric mixture of a compound having an -OCO- group or an -OH group by liquid chromatography. As a filler grafted with an optically active compound for directly separating and analyzing an enantiomeric mixture of a compound having an asymmetric carbon by liquid chromatography, for example, Davankov et al. grafted optically active proline. A method using a ligand exchange using a filler, a method using a charge transfer complex using a filler grafted with an optically active compound lacking Ï electrons by Gil-Av, etc., a method using a charge transfer complex using a filler grafted with an optically active N-acylated amino acid by Hara et al. Separation of N-acylated amino acid esters and N-acylated dipeptide esters using packing materials or Pirkle
3,5-dinitrobenzoylated amino acids using optically active 1-(9-anthryl)trifluoroethanol-grafted fillers by et al.
Separation of amines, oxyacids, sulfoxides, etc. and separation of aromatic alcohols using fillers grafted with 3,5-dinitrobenzoylated optically active phenylglycine have been reported. However, these methods are limited to a narrow range of compounds that can be separated, the degree of separation is small, and it is difficult to produce grafted fillers, making it difficult to produce fillers with reproducible performance. It is difficult to obtain a filler, and it is difficult to say that any of them are practical fillers. Under such circumstances, the present inventors have continued to conduct intensive studies with the aim of developing a grafted filler that is applicable to a wide range of compounds that can be analyzed, is relatively easy to manufacture, and is chemically stable and practical. As a result, optically active pheniglycine acylated with an optically active chrysanthemum acid or α-(4-chlorophenyl)isovaleric acid residue containing an asymmetric carbon was grafted onto an inorganic carrier having a hydroxyl group on its surface. -NH- group bonded to the asymmetric carbon, -
It not only shows excellent effects in separating enantiomeric mixtures of compounds having CONH-, -OCO-, or -OH groups, but also can be easily produced by standard chemical reactions and is chemically stable. We have discovered that these are extremely useful fillers, leading to the present invention. That is, the present invention combines optically active phenylglycine acylated with optically active chrysanthemum acid or α-(4-chlorophenyl)isovaleric acid containing an asymmetric carbon onto an inorganic carrier having a hydroxyl group on its surface. A chromatographic packing material grafted with an optically active organosilane formed by bonding an aminoalkylsilane, and -NH- bonded to an asymmetric carbon using the same as a stationary phase of liquid chromatography.
A method is provided for separating and analyzing enantiomeric mixtures of compounds having -CONH, -OCO- or -OH groups. The present invention will be described in further detail. As the organosilane grafted in the present invention, for example, the general formula [] [In the formula, R 1 , R 2 and R 3 are selected from an alkyl group, an alkoxyl group, a hydroxyl group, or a halogen atom, and at least one is an alkoxyl group or a halogen atom. n is an integer from 2 to 4. A is optically active 3-(2-methyl-1
-propenyl)-2,2-dimethyl-1-cyclopropyl group or optically active 1-(4-chlorophenyl)-isobutyl group. * represents an asymmetric carbon] Optically active N-acylated phenylglycine derivatives can be mentioned. Further, as the aminoalkylsilane component, Ï-aminoalkylalkoxysilane or Ï-aminoalkylhalogenosilane is preferable, and examples thereof include γ-aminopropyltriethoxysilane and γ-aminopropyltrichlorosilane. In the present invention, the inorganic carrier having hydroxyl groups on its surface is preferably a silica-containing carrier such as silica gel, and the carrier may have any shape such as spherical or crushed. In order to obtain this, it is preferable to use fine particles with as uniform a particle size as possible. Various grafting methods can be employed to prepare the novel chromatographic packing material of the present invention, including the following methods. An inorganic carrier having a hydroxyl group on its surface is reacted with an aminoalkylsilane to introduce an aminoalkylsilyl residue onto the surface of the inorganic carrier,
A method of reacting this with optically active phenylglycine acylated with an optically active chrysanthemum acid or α-(4-chlorophenyl)isovaleric acid residue to cause dehydration condensation. More specifically, an inorganic carrier having a hydroxyl group on its surface has the general formula [] [In the formula, R 1 , R 2 , R 3 , and n have the same meanings as above. ] The aminoalkylsilane represented by the formula [] is reacted by a known method to introduce an aminoalkylsilyl residue onto the surface of the inorganic carrier, and then the general formula [] [wherein A and * have the same meanings as above. ] An optically active N-acylated phenylglycine having an asymmetric carbon represented by, for example, N-chrysanthemoylphenylglycine, N-{α-(4-chlorophenyl)isovaleroyl}phenylglycine, etc. is reacted, The desired filling can be obtained by dehydration condensation. In addition, optically active N- having an asymmetric carbon shown in the above general formula []
Acylated phenylglycine can be synthesized by commonly used methods, such as primary chrysanthemum acid or α
-(4-chlorophenyl)isovaleric acid is used as its acid chloride, and it is obtained by reacting the acid chloride with pheniglycine in the presence of a dehydrochlorination agent. A method in which an organosilane obtained by reacting optically active N-acylated phenylglycine with an aminoalkylsilane is grafted onto an inorganic carrier having a hydroxyl group on its surface. More specifically, N-acylated phenylglycine represented by the general formula [] is combined with the general formula []
The desired filler can be obtained by grafting an organosilane represented by the general formula [] obtained by reacting an aminoalkylsilane represented by the following onto an inorganic carrier such as silica gel. The packing material having an optically active N-acylated phenylglycine residue obtained according to the present invention is packed into a chromatography column according to a conventional method and used as a stationary phase in liquid chromatography. In liquid chromatography using this stationary phase, by selecting appropriate elution conditions, especially the commonly used normal phase partition conditions, -
NH- group, -CONH- group, -OCO- group or -OH
Separation and analysis of a mixture of enantiomers of a compound having a group can be performed with good resolution and in a short time. Example 1 Silica gel (particle size 10 ÎŒm, pore size 60 Ã
, surface area 500
m 2 /g) 10g was dried under reduced pressure at 130°C for 4 hours, and then 20g of 3-aminopropyltriethoxysilane was added.
Add to 200ml of dehydrated toluene solution and heat at 60â.
Stir for 6 hours. The reaction mixture was filtered, and the residue was washed with 100 ml of acetone and dried to obtain 3-aminopropyl silylated silica gel (APS). The elemental analysis values of this product were N: 1.20% and C: 3.40%, which corresponds to about 0.90 mmol of 3-aminopropyl group grafted to 1 g of silica gel. Separately, dissolve 10 g of D-phenylglycine in 33 ml of 2N sodium hydroxide solution, add 20 ml of ethyl ether, and while stirring vigorously under ice-cooling, dissolve 15 g of (+)-trans-chrysanthemum acid chloride and 40 ml of 2N sodium hydroxide solution. Add in 7 portions, approximately every 15 minutes. After stirring vigorously for another 2 hours at room temperature, the reaction solution was washed twice with 50 ml of ethyl ether, acidified with 6N hydrochloric acid, and the resulting oil was washed with 100 ml of ethyl acetate.
Extract 3 times. Wash the extract twice with 100ml of water,
After dehydration over anhydrous sodium sulfate and concentration under reduced pressure, recrystallization from a mixture of ethyl acetate and n-hexane yielded N-(+)-trans-chrysanthemoyl-D.
-15 g of phenylglycine was obtained as white crystals. Melting point: 76-80â Optical rotation: [α] 20 D = -38.8ã (c = 2%, chloroform) Elemental analysis values Carbon (%) Hydrogen (%) Nitrogen (%) Calculated value 71.74 7.70 4.65 Actual value 71.58 7.65 4.58 Next, 12 g of this compound and 4.6 g of N-hydroxysuccinimide are dissolved in 100 ml of dehydrated tetrahydrofuran, and while cooling on ice and stirring vigorously, 8.3 g of dicyclohexylcarbodiimide is dissolved in 20 ml of dehydrated tetrahydrofuran and added dropwise over 30 minutes. After stirring for 2 hours under ice-cooling and further stirring for 3 hours at room temperature, the precipitate was removed by filtration, and the solvent was distilled off under reduced pressure. The residue was dissolved in 150 ml of ethyl acetate, washed twice with 50 ml of water, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and then recrystallized from a mixture of ethyl acetate and n-hexane to obtain the formula 12 g of the compound represented by was obtained as white crystals. Melting point: 80-85â Optical rotation: [α] 20 D = 122.9ã (c = 2%, chloroform) Elemental analysis values Carbon (%) Hydrogen (%) Nitrogen (%) Calculated value 66.32 6.58 7.03 Actual value 66.53 6.31 6.99 Next, take 6 g of this compound, suspend 3 g of the aminopropyl silylated silica gel (APS) in 30 ml of dehydrated tetrahydrofuran, add to the sufficiently degassed liquid under reduced pressure, and heat at room temperature for 5 hours, then at 50°C.
Stir gently for 5 hours. After cooling to room temperature, the desired filler was washed three times with 30 ml of tetrahydrofuran, then twice with 30 ml of methanol, and then twice with 30 ml of ethiether, dried, and grafted with N-(+)-trans-chrysanthemoyl-phenylglycine. I got it. The elemental analysis value of this item is N: 1.74
%, C: 13.3%, which is N-(+)-trans-chrysanthemoyl-D per 1 g of silica gel.
- indicates that approximately 0.53 mmol of phenylglycine was grafted. The thus obtained packing material was slurried packed into a stainless steel column with an inner diameter of 4 mm and a length of 30 cm, and (±)-1-(4-chlorophenyl)-4,4-dimethyl-2-( 1, 2, 4
-triazol-1-yl)-1-penten-3
-ol was analyzed and the chromatogram shown in Figure 1 was obtained. Temperature: room temperature Mobile phase: hexane/1,2-dichloroethane/
Ethanol (350:40:4) Flow rate: 1.0ml/min Detector: Ultraviolet absorption meter (wavelength 254nm) In Figure 1, peak number (1)(-)-1-(4-chlorophenyl)-4,4- Dimethyl-2-(1,2,
4-triazol-1-yl)-1-pentene-
3-ol, (2) is (+)-1-(4-chlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol. each peak. The time required for peak (1) to elute is approximately 14 minutes, the separation factor is 1.22, and the time required for peak (1) and (2) to elute is approximately 14 minutes.
The area ratio of the peaks was 50:50. Example 2 (+)-α-(4-chlorophenyl)isovaleric acid
17.0g in n-hexane/toluene mixture (6:1)
Dissolve in 70ml, add 9mg of dimethylforma and add 40ml
Warm to â. To this, 11.5 g of thionyl chloride was added dropwise over 1 hour, and after stirring at 40°C for 5 hours, the solvent was distilled off under reduced pressure at room temperature, resulting in approximately 17.5 g of (+)-α-(4-clofeny)isovaleric acid chloride. get. Dissolve 9.5 g of D-phenylglycine in 32 ml of 2N sodium hydroxide solution, add 20 ml of ethyl ether, and stir vigorously under ice cooling to dissolve the above (+)
-Approximately 17.5 g of α-(4-chlorophenyl)isovaleric acid chloride and 35 ml of 2N sodium hydroxide solution in 10
After addition in 7 portions at ~15 minute intervals and stirring vigorously at room temperature for another 2 hours, the reaction mixture was washed twice with 50 ml of ethyl ether, acidified with 6N hydrochloric acid, and the resulting oil was diluted with 100 ml of ethyl acetate for 30 minutes. Extract times. The extract was washed twice with 100 ml of water, dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. After adding 200 ml of n-hexane to the residue, stirring and washing, the lower layer was taken and the solvent was distilled off under reduced pressure. 21 g of the compound represented by was obtained. Melting point: 68-70â Optical rotation: [α] 20 D = -105.2ã (c = 2.2%, tetrahydrofuran) Elemental analysis values Carbon (%) Hydrogen (%) Nitrogen (%) Chlorine (%) Calculated value 65.99 5.83 4.05 10.25 Actual value 65.49 5.99 3.79 10.41 Next, take 4 g of this compound, dissolve it in 40 ml of dehydrated tetrahydrofuran, and add 1.5 g of this compound while stirring under ice cooling.
-ethoxycarbonyl-2-ethoxy-1,2-
After adding 3.2 g of dihydroquinoline and stirring for 1 hour under ice cooling, 2.5 g of 3-aminopropylsilylated silica gel (APS) obtained in Example 1 was added.
After thoroughly deaerating under reduced pressure, the mixture was gently stirred at room temperature for one day and night. The reaction mixture was washed 4 times with 30 ml of tetrahydrofuran, then twice with 30 ml of methanol, and then twice with 30 ml of ethyl ether, dried, and N-{(+)-
α-(4-chlorophenyl)isovaleroyl}-D
- A desired filler grafted with phenylglycine was obtained. The elemental analysis value of this item is N: 1.26%,
C: 8.72%, which is N- per 1g of silica gel.
This shows that about 0.34 mmol of {(+)-α-(4-chlorophenyl)isovaleroyl}-D-phenylglycine was grafted. The thus obtained packing material was slurried packed into a stainless steel column with an inner diameter of 4 mm and a length of 25 cm.
N-3,5-dinitrobenzoyl-
(R,S)-1-cyclohexylethylamine was analyzed and the chromatogram shown in Figure 2 was obtained. Temperature: Room temperature Mobile phase: n-hexane/1,2-dichloroethane/ethanol (100:20:1) Flow rate: 1.0ml/min Detector: Ultraviolet absorption meter (wavelength: 254nm) Peak number (1) in Figure 2 ) is N-3,5-dinitrobenzoyl-(S)-1-cyclohexylethylamine, (2) is N-3,5-dinitrobenzoyl-(R)
-1-Cyclohexylethylamine peaks. The time required for peak (1) to elute was approximately 10 minutes, the fraction coefficient was 1.20, and the area ratio of peaks (1) and (2) was 50:50. Comparative Example N-(+)-trans-chrysanthemoyl-D of the present invention obtained in Examples 1 and 2, respectively
-Silica gel grafted with phenylglycine (hereinafter abbreviated as CHR-PHG-Si), N-{(+)-α
-(4-chlorophenyl)isovaleroyl}-D-
Silica gel grafted with phenylglycine (hereinafter abbreviated as CPI-PHG-Si) and JP-A-56-1350
N-formyl- produced according to Example 1 of the publication
Silica gel grafted with L-valine (hereinafter referred to as
FVA) was packed into a stainless steel column with an inner diameter of 4 mm and a length of 25 cm as a slurry, and the enantiomers of the following compounds were analyzed under the following conditions and the separation performance of each was compared. The inventive filler is
N-3,5-dinitrobenzoylated amino acid ester, N-acylated amine compared to FVA,
Excellent performance was demonstrated in the separation of enantiomers of carboxylic acid anilides. Temperature: Room temperature Flow rate: 1.0ml/min Detector: Ultraviolet absorption meter (wavelength: 254nm) [Table]
å³âïŒåã³å³âïŒã¯ããããå®æœäŸïŒããã³ïŒ
ã«ãããŠåŸãããã¯ãããã°ã©ã ã§ããã瞊軞ã¯
匷床ã暪軞ã¯ä¿ææéãè¡šãã
Figure-1 and Figure-2 are Examples 1 and 2, respectively.
This is a chromatogram obtained in , where the vertical axis represents intensity and the horizontal axis represents retention time.
Claims (1)
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åææ³ã[Claims] 1. General formula [] [In the formula, R 1 , R 2 and R 3 are selected from an alkyl group, an alkoxyl group, a hydroxyl group, or a halogen atom, and at least one is an alkoxyl group or a halogen atom. n is an integer from 2 to 4. A is optically active 3-(2-methyl-1
-propenyl)-2,2-dimethyl-1-cyclopropyl group or optically active 1-(4-chlorophenyl)-isobutyl group. A chromatographic packing material in which an optically active organosilane represented by *represents an asymmetric carbon is grafted onto an inorganic carrier having hydroxyl groups on its surface. 2. The chromatographic packing material according to claim 1, wherein the inorganic carrier having hydroxyl groups on its surface is silica gel. 3 In the above general formula [], R 1 , R 2 and R 3
The chromatographic packing material according to claim 1 or 2, wherein is an ethoxy group and n is 3. 4 In the above general formula [], R 1 , R 2 and R 3
The chromatographic packing material according to claim 1 or 2, wherein is Cl and n is 3. 5 General formula [] [In the formula, R 1 , R 2 and R 3 are selected from an alkyl group, an alkoxyl group, a hydroxyl group, or a halogen atom, and at least one is an alkoxyl group or a halogen atom. n is an integer from 2 to 4. A is optically active 3-(2-methyl-1
-propenyl)-2,2-dimethyl-1-cyclopropyl group or optically active 1-(4-chlorophenyl)-isobutyl group. An optically active organosilane represented by *represents an asymmetric carbon is grafted onto an inorganic support having a hydroxyl group on its surface. Using a chromatographic packing material, an -NH- group is bonded to an asymmetric carbon. , âCONHâ
A liquid chromatography analysis method characterized by separating and analyzing a mixture of enantiomers of a compound having a -OCO- group or an -OH group. 6. The analytical method according to claim 5, which uses a chromatographic packing material in which the inorganic carrier having hydroxyl groups on its surface is silica gel. 7 In the above general formula [], R 1 , R 2 and R 3
The analytical method according to claim 5 or 6, which uses a chromatographic packing material in which is an ethoxy group and n is 3. 8 In the above general formula [], R 1 , R 2 and R 3
The analytical method according to claim 5 or 6, which uses a chromatographic packing material in which is a Cl group and n is 3.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57131378A JPS5920852A (en) | 1982-07-27 | 1982-07-27 | Chromatographic filler with optically active acylated amino acid being grafted and separation method of enantiomeric mixture using the same |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP57131378A JPS5920852A (en) | 1982-07-27 | 1982-07-27 | Chromatographic filler with optically active acylated amino acid being grafted and separation method of enantiomeric mixture using the same |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5920852A JPS5920852A (en) | 1984-02-02 |
JPH0440660B2 true JPH0440660B2 (en) | 1992-07-03 |
Family
ID=15056541
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP57131378A Granted JPS5920852A (en) | 1982-07-27 | 1982-07-27 | Chromatographic filler with optically active acylated amino acid being grafted and separation method of enantiomeric mixture using the same |
Country Status (1)
Country | Link |
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JP (1) | JPS5920852A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS627934A (en) * | 1985-07-03 | 1987-01-14 | Hitachi Ltd | Variable displacement type turbocharger |
JP2538618B2 (en) * | 1987-10-13 | 1996-09-25 | æäº å | Separation agent |
-
1982
- 1982-07-27 JP JP57131378A patent/JPS5920852A/en active Granted
Also Published As
Publication number | Publication date |
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JPS5920852A (en) | 1984-02-02 |
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