CN101353312B - 苯甘氨酸衍生物的合成 - Google Patents
苯甘氨酸衍生物的合成 Download PDFInfo
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- CN101353312B CN101353312B CN2008101205624A CN200810120562A CN101353312B CN 101353312 B CN101353312 B CN 101353312B CN 2008101205624 A CN2008101205624 A CN 2008101205624A CN 200810120562 A CN200810120562 A CN 200810120562A CN 101353312 B CN101353312 B CN 101353312B
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- alcohol
- propyl
- wormwood
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- 150000005331 phenylglycines Chemical class 0.000 title claims abstract description 12
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000010189 synthetic method Methods 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 22
- 235000015320 potassium carbonate Nutrition 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 14
- -1 methoxyl group Chemical group 0.000 claims description 12
- 239000004471 Glycine Substances 0.000 claims description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 7
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 8
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 abstract description 4
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical group OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 239000012535 impurity Substances 0.000 abstract description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- 239000010842 industrial wastewater Substances 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 239000000047 product Substances 0.000 description 33
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 7
- 230000006837 decompression Effects 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000000967 suction filtration Methods 0.000 description 7
- 238000010792 warming Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- 0 *c1ccc(C(C(O)=O)N)cc1 Chemical compound *c1ccc(C(C(O)=O)N)cc1 0.000 description 2
- FWALJUXKWWBNEO-UHFFFAOYSA-N 2-(4-chloroanilino)acetic acid Chemical compound OC(=O)CNC1=CC=C(Cl)C=C1 FWALJUXKWWBNEO-UHFFFAOYSA-N 0.000 description 2
- OREWWYYIIPPBBW-UHFFFAOYSA-N 2-phenyl-2-(phenylmethoxyamino)acetic acid Chemical compound C(C1=CC=CC=C1)ONC(C1=CC=CC=C1)C(=O)O OREWWYYIIPPBBW-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005267 amalgamation Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000002398 materia medica Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 229910001950 potassium oxide Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- DHGFMVMDBNLMKT-UHFFFAOYSA-N propyl 3-oxobutanoate Chemical compound CCCOC(=O)CC(C)=O DHGFMVMDBNLMKT-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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CN2008101205624A CN101353312B (zh) | 2008-08-20 | 2008-08-20 | 苯甘氨酸衍生物的合成 |
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CN2008101205624A CN101353312B (zh) | 2008-08-20 | 2008-08-20 | 苯甘氨酸衍生物的合成 |
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CN101353312A CN101353312A (zh) | 2009-01-28 |
CN101353312B true CN101353312B (zh) | 2011-12-14 |
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CN2008101205624A Active CN101353312B (zh) | 2008-08-20 | 2008-08-20 | 苯甘氨酸衍生物的合成 |
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Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN102165950B (zh) * | 2011-03-10 | 2014-02-26 | 浙江大学 | 苯基甘氨酸衍生物对大肠杆菌有抑菌和杀菌活性 |
CN102144992B (zh) * | 2011-03-10 | 2013-04-10 | 浙江大学 | 苯基甘氨酸衍生物制备对金黄色葡萄球菌有抑菌和杀菌活性的抗菌剂的用途 |
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Application publication date: 20090128 Assignee: CHANGYI HANXING MEDICAL SCIENCE CO.,LTD. Assignor: HENGDIAN GROUP JIAYUAN CHEMICAL INDUSTRY Co.,Ltd.|Zhejiang Apeloa Medical Technology Co.,Ltd. Contract record no.: 2014370000013 Denomination of invention: Phenylglycine derivatives synthesis Granted publication date: 20111214 License type: Exclusive License Record date: 20140307 |
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Effective date of registration: 20200618 Address after: 322118 Hengdian Industrial Zone, Jinhua, Zhejiang, China, Dongyang Co-patentee after: APELOA PHARMACEUTICAL Co.,Ltd. Patentee after: ZHEJIANG APELOA JIAYUAN PHARMACEUTICAL Co.,Ltd. Address before: 322118 Hengdian Industrial Zone, Jinhua, Zhejiang, China, Dongyang Patentee before: ZHEJIANG APELOA JIAYUAN PHARMACEUTICAL Co.,Ltd. |
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Denomination of invention: Synthesis of Phenylglycine Derivatives Effective date of registration: 20220921 Granted publication date: 20111214 Pledgee: Dongyang sub branch of Bank of China Ltd. Pledgor: ZHEJIANG APELOA JIAYUAN PHARMACEUTICAL Co.,Ltd. Registration number: Y2022330002348 |
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Date of cancellation: 20230925 Granted publication date: 20111214 Pledgee: Dongyang sub branch of Bank of China Ltd. Pledgor: ZHEJIANG APELOA JIAYUAN PHARMACEUTICAL Co.,Ltd. Registration number: Y2022330002348 |
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Denomination of invention: Synthesis of phenylglycine derivatives Effective date of registration: 20231024 Granted publication date: 20111214 Pledgee: Dongyang sub branch of Bank of China Ltd. Pledgor: ZHEJIANG APELOA JIAYUAN PHARMACEUTICAL Co.,Ltd. Registration number: Y2023980062462 |
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