CN101190934B - 相转移法制备齐多夫定叠氮中间体的方法 - Google Patents
相转移法制备齐多夫定叠氮中间体的方法 Download PDFInfo
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- CN101190934B CN101190934B CN2006101187881A CN200610118788A CN101190934B CN 101190934 B CN101190934 B CN 101190934B CN 2006101187881 A CN2006101187881 A CN 2006101187881A CN 200610118788 A CN200610118788 A CN 200610118788A CN 101190934 B CN101190934 B CN 101190934B
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- Prior art keywords
- zidovudine
- phase
- phase transition
- oxygen bridge
- sodiumazide
- 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.)
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- 229960002555 zidovudine Drugs 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 23
- 230000007704 transition Effects 0.000 title claims description 7
- -1 Zidovudine azide Chemical class 0.000 title abstract 3
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims abstract description 22
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 9
- 239000003444 phase transfer catalyst Substances 0.000 claims abstract description 8
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 3
- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 11
- 239000001301 oxygen Substances 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical group [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 5
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical group [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 5
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 3
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 3
- AJSHDAOMUKXVDC-UHFFFAOYSA-N butan-1-amine;sulfuric acid Chemical compound CCCC[NH3+].OS([O-])(=O)=O AJSHDAOMUKXVDC-UHFFFAOYSA-N 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 230000035484 reaction time Effects 0.000 abstract description 3
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000010792 warming Methods 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 4
- 230000006837 decompression Effects 0.000 description 4
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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- Saccharide Compounds (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2006101187881A CN101190934B (zh) | 2006-11-27 | 2006-11-27 | 相转移法制备齐多夫定叠氮中间体的方法 |
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CN2006101187881A CN101190934B (zh) | 2006-11-27 | 2006-11-27 | 相转移法制备齐多夫定叠氮中间体的方法 |
Publications (2)
Publication Number | Publication Date |
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CN101190934A CN101190934A (zh) | 2008-06-04 |
CN101190934B true CN101190934B (zh) | 2010-12-15 |
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CN2006101187881A Active CN101190934B (zh) | 2006-11-27 | 2006-11-27 | 相转移法制备齐多夫定叠氮中间体的方法 |
Country Status (1)
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Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103443095B (zh) * | 2011-11-07 | 2016-01-20 | 上海迪赛诺药业有限公司 | 制备齐多夫定及其中间体的方法 |
CN103201278B (zh) * | 2011-11-07 | 2016-01-20 | 上海迪赛诺药业有限公司 | 制备齐多夫定及其中间体的方法 |
CN104844672A (zh) * | 2015-04-09 | 2015-08-19 | 苏州华诺医药有限公司 | 制备齐多夫定及其中间体的方法 |
CN113461759A (zh) * | 2021-07-02 | 2021-10-01 | 华东理工大学 | 基于连续流微反应技术合成齐多夫定叠氮化中间体的方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5124442A (en) * | 1989-10-27 | 1992-06-23 | Universite Pierre Et Marie Curie (Paris Vi) | Process for preparing azt (3'-azido-3'-deoxy-thymidine) and related compounds |
-
2006
- 2006-11-27 CN CN2006101187881A patent/CN101190934B/zh active Active
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5124442A (en) * | 1989-10-27 | 1992-06-23 | Universite Pierre Et Marie Curie (Paris Vi) | Process for preparing azt (3'-azido-3'-deoxy-thymidine) and related compounds |
Non-Patent Citations (2)
Title |
---|
刘世领等.齐多夫定的合成.中国医药工业杂志.2006,37(9),577-579. * |
王乃兴等.有机合成中的相转移催化作用.化学世界.1994,(9),450-453. * |
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Address after: 201300, No. 9125, Shanghai South Road, Nanhui District, Shanghai Patentee after: SHANGHAI DESANO CHEMICAL PHARMACEUTICAL Co.,Ltd. Patentee after: SHANGHAI ACEBRIGHT PHARMACEUTICALS GROUP Co.,Ltd. Patentee after: SHANGHAI DESANO PHARMACEUTICALS INVESTMENT Co.,Ltd. Address before: 201300, No. 9125, Shanghai South Road, Nanhui District, Shanghai Patentee before: SHANGHAI DESANO CHEMICAL PHARMACEUTICAL Co.,Ltd. Patentee before: SHANGHAI ACEBRIGHT PHARMACEUTICALS GROUP Co.,Ltd. Patentee before: SHANGHAI DESANO PHARMACEUTICALS INVESTMENT Co.,Ltd. |
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