CN1293039C - Preparation of [(S)-(-)-alpha-methylamino phenylketone]2.(2R,3R)-tartaric acid derivative - Google Patents
Preparation of [(S)-(-)-alpha-methylamino phenylketone]2.(2R,3R)-tartaric acid derivative Download PDFInfo
- Publication number
- CN1293039C CN1293039C CN 200410024865 CN200410024865A CN1293039C CN 1293039 C CN1293039 C CN 1293039C CN 200410024865 CN200410024865 CN 200410024865 CN 200410024865 A CN200410024865 A CN 200410024865A CN 1293039 C CN1293039 C CN 1293039C
- Authority
- CN
- China
- Prior art keywords
- methylamino propiophenone
- methylamino
- tartaric acid
- propiophenone
- alcohol
- 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
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 21
- 239000012046 mixed solvent Substances 0.000 claims abstract description 14
- LPLLVINFLBSFRP-MRVPVSSYSA-N (R)-methcathinone Chemical compound CN[C@H](C)C(=O)C1=CC=CC=C1 LPLLVINFLBSFRP-MRVPVSSYSA-N 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 238000007796 conventional method Methods 0.000 claims abstract 2
- LPLLVINFLBSFRP-UHFFFAOYSA-N 2-methylamino-1-phenylpropan-1-one Chemical compound CNC(C)C(=O)C1=CC=CC=C1 LPLLVINFLBSFRP-UHFFFAOYSA-N 0.000 claims description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 150000002148 esters Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000012452 mother liquor Substances 0.000 claims description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 7
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 7
- 230000006340 racemization Effects 0.000 claims description 7
- DDLRQJKPTRBKAM-UHFFFAOYSA-N 1-O-benzoyl 4-O-methyl 2,3-dihydroxybutanedioate Chemical compound C(=O)(OC)C(O)C(O)C(=O)OC(C1=CC=CC=C1)=O DDLRQJKPTRBKAM-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 6
- LIKCOUQZUAUHIZ-UHFFFAOYSA-N O.C(=O)(OC)C(O)C(O)C(=O)OC(C1=CC=CC=C1)=O Chemical compound O.C(=O)(OC)C(O)C(O)C(=O)OC(C1=CC=CC=C1)=O LIKCOUQZUAUHIZ-UHFFFAOYSA-N 0.000 claims description 6
- 238000005194 fractionation Methods 0.000 claims description 6
- 150000003899 tartaric acid esters Chemical class 0.000 claims description 6
- 229940095064 tartrate Drugs 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- UUDLQDCYDSATCH-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;hydrate Chemical compound O.OC(=O)C(O)C(O)C(O)=O UUDLQDCYDSATCH-UHFFFAOYSA-N 0.000 claims description 3
- 239000010410 layer Substances 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- JPNUKQTTWJPNGS-RMTNWKGQSA-N (2s)-2-(methylamino)-1-phenylpropan-1-one;(2r)-2-(methylamino)-1-phenylpropan-1-one Chemical compound CN[C@H](C)C(=O)C1=CC=CC=C1.CN[C@@H](C)C(=O)C1=CC=CC=C1 JPNUKQTTWJPNGS-RMTNWKGQSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- PTAPBGKYBVWNJY-UHFFFAOYSA-N 2,3-dibenzoyl-2,3-dihydroxybutanedioic acid;hydrate Chemical compound O.C=1C=CC=CC=1C(=O)C(O)(C(O)=O)C(O)(C(=O)O)C(=O)C1=CC=CC=C1 PTAPBGKYBVWNJY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229910052728 basic metal Inorganic materials 0.000 claims description 2
- 150000003818 basic metals Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 238000000638 solvent extraction Methods 0.000 claims description 2
- LPLLVINFLBSFRP-QMMMGPOBSA-N (S)-methcathinone Chemical compound CN[C@@H](C)C(=O)C1=CC=CC=C1 LPLLVINFLBSFRP-QMMMGPOBSA-N 0.000 abstract description 11
- 230000003287 optical effect Effects 0.000 abstract description 11
- 238000010438 heat treatment Methods 0.000 abstract description 8
- 239000003513 alkali Substances 0.000 abstract description 4
- 239000000047 product Substances 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 3
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 abstract description 3
- KWGRBVOPPLSCSI-PSASIEDQSA-N (1s,2r)-2-(methylamino)-1-phenylpropan-1-ol Chemical compound CN[C@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-PSASIEDQSA-N 0.000 abstract description 2
- 239000007795 chemical reaction product Substances 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 5
- -1 (S)-(-)-α-methylamino Propiophenone (1R)-(-)-camphorsulfonic acid Chemical compound 0.000 description 3
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- MIOPJNTWMNEORI-MHPPCMCBSA-N [(4r)-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl]methanesulfonic acid Chemical compound C1C[C@]2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-MHPPCMCBSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- LSPHULWDVZXLIL-LDWIPMOCSA-N (?)-Camphoric acid Chemical compound CC1(C)[C@@H](C(O)=O)CC[C@@]1(C)C(O)=O LSPHULWDVZXLIL-LDWIPMOCSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- OCQAXYHNMWVLRH-UHFFFAOYSA-N 2,3-dibenzoyl-2,3-dihydroxybutanedioic acid Chemical group C=1C=CC=CC=1C(=O)C(O)(C(O)=O)C(O)(C(=O)O)C(=O)C1=CC=CC=C1 OCQAXYHNMWVLRH-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-OMNKOJBGSA-N [(4s)-7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl]methanesulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-OMNKOJBGSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000005251 capillar electrophoresis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (5)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200410024865 CN1293039C (en) | 2004-06-02 | 2004-06-02 | Preparation of [(S)-(-)-alpha-methylamino phenylketone]2.(2R,3R)-tartaric acid derivative |
PCT/CN2005/000744 WO2005118524A1 (en) | 2004-06-02 | 2005-05-27 | Process for preparing [(s)-(-)alpha-methylamino phenylacetone]2 (2r, 3r)-tartaric acid derivates |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN 200410024865 CN1293039C (en) | 2004-06-02 | 2004-06-02 | Preparation of [(S)-(-)-alpha-methylamino phenylketone]2.(2R,3R)-tartaric acid derivative |
Publications (2)
Publication Number | Publication Date |
---|---|
CN1583714A CN1583714A (en) | 2005-02-23 |
CN1293039C true CN1293039C (en) | 2007-01-03 |
Family
ID=34601012
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 200410024865 Expired - Lifetime CN1293039C (en) | 2004-06-02 | 2004-06-02 | Preparation of [(S)-(-)-alpha-methylamino phenylketone]2.(2R,3R)-tartaric acid derivative |
Country Status (2)
Country | Link |
---|---|
CN (1) | CN1293039C (en) |
WO (1) | WO2005118524A1 (en) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101870660A (en) * | 2010-05-10 | 2010-10-27 | 青海省青海湖药业有限公司 | Preparation method of L-(-)-ephedrine chloride and d-(+)-pseudoephedrine hydrochloride |
CN104119240A (en) * | 2013-04-23 | 2014-10-29 | 中国人民解放军军事医学科学院毒物药物研究所 | Preparation method for (S)-(-)-alpha-methylaminopropiophenone |
CN104725259B (en) * | 2013-12-19 | 2017-01-18 | 上海医药工业研究院 | Preparation method for levodopa intermediate derivative |
CN113024391A (en) * | 2021-04-09 | 2021-06-25 | 北京旋光普利生物医药科技开发有限公司 | Preparation of (S) - (-) -alpha-methylaminopropiophenone |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE538932A (en) * | 1954-06-15 | |||
US5227526A (en) * | 1992-06-16 | 1993-07-13 | Mallinckrodt Specialty Chemicals Company | Resolution of 3-dimethylamino-2-methylpropiophenone (3-DAMP) |
CN1211349C (en) * | 1999-12-06 | 2005-07-20 | 赤峰艾克制药科技股份有限公司 | Process for preparing alpha-amidophenylketone with optical activity |
CN1265391A (en) * | 2000-01-31 | 2000-09-06 | 李健府 | Preparation of levorotary Alpha-methylamino-phenylacetone and repeated usage of separating agent |
CN1267664A (en) * | 2000-03-14 | 2000-09-27 | 李健府 | Preparation of levorotary alpha-methylamino phenyl acetone |
-
2004
- 2004-06-02 CN CN 200410024865 patent/CN1293039C/en not_active Expired - Lifetime
-
2005
- 2005-05-27 WO PCT/CN2005/000744 patent/WO2005118524A1/en active Application Filing
Also Published As
Publication number | Publication date |
---|---|
CN1583714A (en) | 2005-02-23 |
WO2005118524A1 (en) | 2005-12-15 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
C56 | Change in the name or address of the patentee | ||
CP01 | Change in the name or title of a patent holder |
Address after: 200040 Beijing West Road, Shanghai, No. 1320 Patentee after: SHANGHAI INSTITUTE OF PHARMACEUTICAL INDUSTRY Patentee after: ZHEJIANG APELOA KANGYU PHARMACEUTICAL Co.,Ltd. Address before: 200040 Beijing West Road, Shanghai, No. 1320 Patentee before: Shanghai Institute of pharmaceutical industry Patentee before: ZHEJIANG KANGYU PHARMACEUTICAL Co.,Ltd. |
|
TR01 | Transfer of patent right | ||
TR01 | Transfer of patent right |
Effective date of registration: 20200714 Address after: No.399, Jiangnan Road, Hengdian Town, Dongyang City, Zhejiang Province Co-patentee after: SHANGHAI INSTITUTE OF PHARMACEUTICAL INDUSTRY Patentee after: APELOA PHARMACEUTICAL Co.,Ltd. Co-patentee after: ZHEJIANG APELOA KANGYU PHARMACEUTICAL Co.,Ltd. Address before: 200040 No. 1320 West Beijing Road, Shanghai Co-patentee before: ZHEJIANG APELOA KANGYU PHARMACEUTICAL Co.,Ltd. Patentee before: SHANGHAI INSTITUTE OF PHARMACEUTICAL INDUSTRY |
|
DD01 | Delivery of document by public notice | ||
DD01 | Delivery of document by public notice |
Addressee: Xu Wei Document name: Notification of Passing Examination on Formalities |
|
CX01 | Expiry of patent term | ||
CX01 | Expiry of patent term |
Granted publication date: 20070103 |