JPS6251689A - 新規な光学活性シランカツプリング剤及びその製造方法 - Google Patents
新規な光学活性シランカツプリング剤及びその製造方法Info
- Publication number
- JPS6251689A JPS6251689A JP60190397A JP19039785A JPS6251689A JP S6251689 A JPS6251689 A JP S6251689A JP 60190397 A JP60190397 A JP 60190397A JP 19039785 A JP19039785 A JP 19039785A JP S6251689 A JPS6251689 A JP S6251689A
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- coupling agent
- proline
- silica gel
- silane coupling
- 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
- 239000006087 Silane Coupling Agent Substances 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 150000003926 acrylamides Chemical class 0.000 claims 1
- 125000005370 alkoxysilyl group Chemical group 0.000 claims 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract description 18
- 229940024606 amino acid Drugs 0.000 abstract description 14
- 150000001413 amino acids Chemical class 0.000 abstract description 13
- 239000000741 silica gel Substances 0.000 abstract description 13
- 229910002027 silica gel Inorganic materials 0.000 abstract description 13
- 239000000463 material Substances 0.000 abstract description 10
- 238000000926 separation method Methods 0.000 abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 9
- 230000003287 optical effect Effects 0.000 abstract description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 229910052802 copper Inorganic materials 0.000 abstract description 4
- 239000010949 copper Substances 0.000 abstract description 4
- 239000000945 filler Substances 0.000 abstract description 4
- 239000002245 particle Substances 0.000 abstract description 4
- 229960002429 proline Drugs 0.000 abstract description 4
- PGECUMPWQLVJCY-UHFFFAOYSA-N 2-methylidene-5-triethoxysilylpentanamide Chemical compound CCO[Si](OCC)(OCC)CCCC(=C)C(N)=O PGECUMPWQLVJCY-UHFFFAOYSA-N 0.000 abstract description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 2
- 238000004128 high performance liquid chromatography Methods 0.000 abstract description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 abstract 2
- 229930182821 L-proline Natural products 0.000 abstract 1
- 239000003125 aqueous solvent Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 235000001014 amino acid Nutrition 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000000524 functional group Chemical group 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000012856 packing Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001261 hydroxy acids Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000004811 liquid chromatography Methods 0.000 description 3
- -1 polysiloxane Polymers 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 2
- 238000006845 Michael addition reaction Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- 239000004793 Polystyrene Substances 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
- 235000002597 Solanum melongena Nutrition 0.000 description 1
- IMGRELTYELUXPL-UHFFFAOYSA-N [SiH3]CCCC(C(=O)N)=C Chemical compound [SiH3]CCCC(C(=O)N)=C IMGRELTYELUXPL-UHFFFAOYSA-N 0.000 description 1
- 150000001371 alpha-amino acids Chemical class 0.000 description 1
- 235000008206 alpha-amino acids Nutrition 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- RUBFCLDQBHUROT-WCCKRBBISA-N copper;(2s)-pyrrolidine-2-carboxylic acid Chemical compound [Cu].OC(=O)[C@@H]1CCCN1 RUBFCLDQBHUROT-WCCKRBBISA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- CQAIPTBBCVQRMD-UHFFFAOYSA-L dipotassium;phosphono phosphate Chemical compound [K+].[K+].OP(O)(=O)OP([O-])([O-])=O CQAIPTBBCVQRMD-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 229940087646 methanolamine Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60190397A JPS6251689A (ja) | 1985-08-29 | 1985-08-29 | 新規な光学活性シランカツプリング剤及びその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60190397A JPS6251689A (ja) | 1985-08-29 | 1985-08-29 | 新規な光学活性シランカツプリング剤及びその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6251689A true JPS6251689A (ja) | 1987-03-06 |
| JPS6341399B2 JPS6341399B2 (enrdf_load_stackoverflow) | 1988-08-17 |
Family
ID=16257473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60190397A Granted JPS6251689A (ja) | 1985-08-29 | 1985-08-29 | 新規な光学活性シランカツプリング剤及びその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6251689A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005079975A1 (en) * | 2004-02-12 | 2005-09-01 | Varian, Inc. | Polar-modified bonded phase materials for chromatographic separations |
| CN113671077A (zh) * | 2021-08-17 | 2021-11-19 | 成都倍特药业股份有限公司 | 丙烯酰氯及其有关物质检测方法 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10847881B2 (en) * | 2019-02-01 | 2020-11-24 | Pc-Tel, Inc. | Dual-band antenna with notched cross-polarization suppression |
-
1985
- 1985-08-29 JP JP60190397A patent/JPS6251689A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005079975A1 (en) * | 2004-02-12 | 2005-09-01 | Varian, Inc. | Polar-modified bonded phase materials for chromatographic separations |
| KR101141105B1 (ko) * | 2004-02-12 | 2012-05-02 | 어질런트 테크놀러지스, 인코포레이티드 | 크로마토그래피 분리용의 극성 변성된 결합 상 물질 |
| CN113671077A (zh) * | 2021-08-17 | 2021-11-19 | 成都倍特药业股份有限公司 | 丙烯酰氯及其有关物质检测方法 |
| CN113671077B (zh) * | 2021-08-17 | 2023-08-18 | 成都倍特药业股份有限公司 | 丙烯酰氯及其有关物质检测方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6341399B2 (enrdf_load_stackoverflow) | 1988-08-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |