BE505140A - - Google Patents
Info
- Publication number
- BE505140A BE505140A BE505140DA BE505140A BE 505140 A BE505140 A BE 505140A BE 505140D A BE505140D A BE 505140DA BE 505140 A BE505140 A BE 505140A
- Authority
- BE
- Belgium
- Prior art keywords
- nitrophenyl
- ethyl acetate
- serine
- derivative
- diol
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 claims description 18
- OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical compound [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 claims description 18
- 150000004696 coordination complex Chemical class 0.000 claims description 14
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- SRTHRWZAMDZJOS-UHFFFAOYSA-N Lithium hydride Chemical compound [H-].[Li+] SRTHRWZAMDZJOS-UHFFFAOYSA-N 0.000 claims description 6
- -1 N-dichloroacetyl - nitrophenyl-serine Chemical compound 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000003638 reducing agent Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 2
- ODWJFOAKNUPQDP-QMMMGPOBSA-N [N+](=O)([O-])N([C@@H](CO)C(=O)O)C1=CC=CC=C1 Chemical compound [N+](=O)([O-])N([C@@H](CO)C(=O)O)C1=CC=CC=C1 ODWJFOAKNUPQDP-QMMMGPOBSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 159
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- 239000000243 solution Substances 0.000 description 49
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 34
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 27
- 239000000203 mixture Substances 0.000 description 26
- 239000000284 extract Substances 0.000 description 23
- 239000012071 phase Substances 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000007792 addition Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 11
- 239000008346 aqueous phase Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000004821 distillation Methods 0.000 description 7
- 239000002024 ethyl acetate extract Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- 230000003287 optical Effects 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- MTCFGRXMJLQNBG-UWTATZPHSA-N D-serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 description 2
- KWGRBVOPPLSCSI-WPRPVWTQSA-N Ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 230000003115 biocidal Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- 229940064005 Antibiotic throat preparations Drugs 0.000 description 1
- 229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 description 1
- 229940042052 Antibiotics for systemic use Drugs 0.000 description 1
- 229940042786 Antitubercular Antibiotics Drugs 0.000 description 1
- 241000220450 Cajanus cajan Species 0.000 description 1
- 229940093922 Gynecological Antibiotics Drugs 0.000 description 1
- 241000155250 Iole Species 0.000 description 1
- MTCFGRXMJLQNBG-REOHCLBHSA-M L-serinate Chemical compound OC[C@H](N)C([O-])=O MTCFGRXMJLQNBG-REOHCLBHSA-M 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- IIMIOEBMYPRQGU-UHFFFAOYSA-L Picoplatin Chemical compound N.[Cl-].[Cl-].[Pt+2].CC1=CC=CC=N1 IIMIOEBMYPRQGU-UHFFFAOYSA-L 0.000 description 1
- KWGRBVOPPLSCSI-WCBMZHEXSA-N Pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 1
- 229960003908 Pseudoephedrine Drugs 0.000 description 1
- YTBSYETUWUMLBZ-QWWZWVQMSA-N Threose Chemical compound OC[C@@H](O)[C@H](O)C=O YTBSYETUWUMLBZ-QWWZWVQMSA-N 0.000 description 1
- 229940024982 Topical Antifungal Antibiotics Drugs 0.000 description 1
- 241001106462 Ulmus Species 0.000 description 1
- 241000209149 Zea Species 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- XKLHJVLEVHZUSV-UHFFFAOYSA-N [H-].[H-].[Li+].[Na+] Chemical compound [H-].[H-].[Li+].[Na+] XKLHJVLEVHZUSV-UHFFFAOYSA-N 0.000 description 1
- WKPYEPGXJHUJGR-UHFFFAOYSA-N [N+](=O)([O-])C(C(CO)NC(C(Cl)Cl)=O)(O)C1=CC=CC=C1 Chemical compound [N+](=O)([O-])C(C(CO)NC(C(Cl)Cl)=O)(O)C1=CC=CC=C1 WKPYEPGXJHUJGR-UHFFFAOYSA-N 0.000 description 1
- LCWCUJFBQGBZBR-UHFFFAOYSA-N [N+](=O)([O-])C1(CC=CC=C1)C(C(CO)N)O Chemical class [N+](=O)([O-])C1(CC=CC=C1)C(C(CO)N)O LCWCUJFBQGBZBR-UHFFFAOYSA-N 0.000 description 1
- ODWJFOAKNUPQDP-QMMMGPOBSA-M [N+](=O)([O-])N([C@@H](CO)C(=O)[O-])C1=CC=CC=C1 Chemical compound [N+](=O)([O-])N([C@@H](CO)C(=O)[O-])C1=CC=CC=C1 ODWJFOAKNUPQDP-QMMMGPOBSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 125000004432 carbon atoms Chemical group C* 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000005824 corn Nutrition 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- KVXNKFYSHAUJIA-UHFFFAOYSA-M ethoxyethane;acetate Chemical compound CC([O-])=O.CCOCC KVXNKFYSHAUJIA-UHFFFAOYSA-M 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940079866 intestinal antibiotics Drugs 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Chemical class [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229940005935 ophthalmologic Antibiotics Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE505140A true BE505140A (US06312121-20011106-C00033.png) |
Family
ID=145772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE505140D BE505140A (US06312121-20011106-C00033.png) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE505140A (US06312121-20011106-C00033.png) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2816915A (en) * | 1953-11-20 | 1957-12-17 | Du Pont | Separation of phenyl-serines |
| DE975296C (de) * | 1953-01-13 | 1961-11-02 | Beiersdorf & Co A G P | Verfahren zur Herstellung von D, L-threo-1-p-Nitrophenyl-2-dichloracetamino-1, 3-propandiol und seiner optischen Antipoden |
-
0
- BE BE505140D patent/BE505140A/fr unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE975296C (de) * | 1953-01-13 | 1961-11-02 | Beiersdorf & Co A G P | Verfahren zur Herstellung von D, L-threo-1-p-Nitrophenyl-2-dichloracetamino-1, 3-propandiol und seiner optischen Antipoden |
| US2816915A (en) * | 1953-11-20 | 1957-12-17 | Du Pont | Separation of phenyl-serines |
