CA1097662A - Process for preparing an optically active benzamide, the optically active benzamide so obtained, and pharmaceutical compositions containing it - Google Patents
Process for preparing an optically active benzamide, the optically active benzamide so obtained, and pharmaceutical compositions containing itInfo
- Publication number
- CA1097662A CA1097662A CA321,673A CA321673A CA1097662A CA 1097662 A CA1097662 A CA 1097662A CA 321673 A CA321673 A CA 321673A CA 1097662 A CA1097662 A CA 1097662A
- Authority
- CA
- Canada
- Prior art keywords
- ethyl
- levo
- methoxy
- sulphamoyl
- proline
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title description 8
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- GNMSLDIYJOSUSW-LURJTMIESA-N N-acetyl-L-proline Chemical compound CC(=O)N1CCC[C@H]1C(O)=O GNMSLDIYJOSUSW-LURJTMIESA-N 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 8
- 229910021529 ammonia Inorganic materials 0.000 claims description 7
- UNRBEYYLYRXYCG-UHFFFAOYSA-N (1-ethylpyrrolidin-2-yl)methanamine Chemical compound CCN1CCCC1CN UNRBEYYLYRXYCG-UHFFFAOYSA-N 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 229910010084 LiAlH4 Inorganic materials 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052987 metal hydride Inorganic materials 0.000 claims description 2
- 150000004681 metal hydrides Chemical class 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 229940050176 methyl chloride Drugs 0.000 claims 1
- 230000021736 acetylation Effects 0.000 abstract description 3
- 238000006640 acetylation reaction Methods 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- -1 amino compound Chemical class 0.000 abstract description 2
- 238000005660 chlorination reaction Methods 0.000 abstract description 2
- 238000005576 amination reaction Methods 0.000 abstract 1
- 230000000506 psychotropic effect Effects 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229960004940 sulpiride Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 3
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- SQAILWDRVDGLGY-UHFFFAOYSA-N 2-methoxy-5-sulfamoylbenzoic acid Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(O)=O SQAILWDRVDGLGY-UHFFFAOYSA-N 0.000 description 1
- KDNIOKSLVIGAAN-UHFFFAOYSA-N 2-sulfamoylbenzoic acid Chemical compound NS(=O)(=O)C1=CC=CC=C1C(O)=O KDNIOKSLVIGAAN-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 241000490229 Eucephalus Species 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 101150007148 THI5 gene Proteins 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057948 magnesium stearate Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT20295/78A IT1095415B (it) | 1978-02-16 | 1978-02-16 | Processo per la produzione di una benzamide otticamente attiva,benzamide otticamente attiva cosi'ottenuta e composizioni |
| IT20295A/78 | 1978-02-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1097662A true CA1097662A (en) | 1981-03-17 |
Family
ID=11165504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA321,673A Expired CA1097662A (en) | 1978-02-16 | 1979-02-16 | Process for preparing an optically active benzamide, the optically active benzamide so obtained, and pharmaceutical compositions containing it |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS54130562A (xx) |
| AT (1) | AT373870B (xx) |
| CA (1) | CA1097662A (xx) |
| CH (1) | CH639951A5 (xx) |
| DE (1) | DE2903891A1 (xx) |
| DK (1) | DK152752C (xx) |
| EG (1) | EG14440A (xx) |
| FR (1) | FR2417498A1 (xx) |
| GB (1) | GB2014990B (xx) |
| GR (1) | GR78220B (xx) |
| IT (1) | IT1095415B (xx) |
| MX (1) | MX5632E (xx) |
| NL (1) | NL190845C (xx) |
| SE (1) | SE430888B (xx) |
| YU (1) | YU41145B (xx) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1141095B (it) * | 1980-11-27 | 1986-10-01 | Ravizza Spa | Processo di risoluzione della sulpiride racema |
| EP0088849A1 (fr) * | 1982-03-11 | 1983-09-21 | Choay S.A. | Isomères lévogyres de composés benzènesulfonamides N-substitués, leur procédé de préparation et compositions pharmaceutiques les contenant |
| SE8602339D0 (sv) * | 1986-05-22 | 1986-05-22 | Astra Laekemedel Ab | An efficient stereoconservative synthesis of 1-substituted (s)- and (r)-2-aminomethylpyrrolidines |
| DE4103451C2 (de) * | 1991-02-02 | 1994-08-25 | Hormosan Kwizda Gmbh | Verwendungen des Wirkstoffes Sulpirid in seiner R- bzw. S-Form |
| AU2002364553A1 (en) * | 2001-12-28 | 2003-07-15 | Farmaceutsko-Hemijska Industrija "Zdravlje" | A process for synthesis of heterocyclic aminoalkyl benzamides |
| ITMI20051943A1 (it) * | 2005-10-14 | 2007-04-15 | Procos Spa | Processo di risoluzione anantiomerica di 2-aminometil-pirrolidine 1-sostitute per ammidazione in presenza di lipasi |
| CL2012000874S1 (es) | 2012-01-31 | 2013-03-22 | Saverglass | Botella de cuerpo paralelepipedico rectangular ahusado orientado de forma vertical, con su parte mas angosta situada en el extremo inferior, tiene todos su bordes curvos, en su extremo superior forma una superficie rectangular con sus lados convexos, la cual esta unida al cuello de botella mediante ligeras pendientes. |
| CN103772256B (zh) * | 2012-10-24 | 2017-10-10 | 江苏天士力帝益药业有限公司 | 一种高纯度舒必利或其光学异构体的制备方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3891671A (en) * | 1968-08-01 | 1975-06-24 | Ile De France | N-(2-pyrrolidyl or piperidyl alkyl)-4-hydroxy benzamides |
| CH605793A5 (xx) * | 1974-03-05 | 1978-10-13 | Ile De France | |
| FR2394529A2 (fr) * | 1977-06-13 | 1979-01-12 | Synthelabo | Methoxy-2 benzamides et leur application en therapeutique |
| FR2393794A2 (fr) * | 1977-06-06 | 1979-01-05 | Synthelabo | Preparation de methoxy-2 benzamides |
| IL52645A (en) * | 1976-08-05 | 1980-02-29 | Synthelabo | Optically active 1 substituted 2 aminomethyl pyrrolidines stereospecifics synthesis thereof and process for the preparation of optically active 2 methoxy n pyrrolidylmethyl benzamides |
| JPS5365875A (en) * | 1976-11-24 | 1978-06-12 | Teijin Ltd | Preparation of benzenesulfone amide derivs. |
-
1978
- 1978-02-16 IT IT20295/78A patent/IT1095415B/it active
-
1979
- 1979-02-01 DE DE19792903891 patent/DE2903891A1/de active Granted
- 1979-02-05 GB GB7903902A patent/GB2014990B/en not_active Expired
- 1979-02-08 FR FR7903216A patent/FR2417498A1/fr active Granted
- 1979-02-12 YU YU308/79A patent/YU41145B/xx unknown
- 1979-02-13 AT AT0110179A patent/AT373870B/de not_active IP Right Cessation
- 1979-02-13 JP JP1441979A patent/JPS54130562A/ja active Pending
- 1979-02-13 MX MX797713U patent/MX5632E/es unknown
- 1979-02-14 EG EG97/79A patent/EG14440A/xx active
- 1979-02-14 CH CH142779A patent/CH639951A5/de not_active IP Right Cessation
- 1979-02-15 SE SE7901337A patent/SE430888B/sv not_active IP Right Cessation
- 1979-02-15 GR GR58375A patent/GR78220B/el unknown
- 1979-02-15 DK DK066579A patent/DK152752C/da not_active IP Right Cessation
- 1979-02-16 NL NL7901251A patent/NL190845C/xx not_active IP Right Cessation
- 1979-02-16 CA CA321,673A patent/CA1097662A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2417498B1 (xx) | 1983-01-21 |
| IT1095415B (it) | 1985-08-10 |
| DE2903891A1 (de) | 1979-08-23 |
| SE7901337L (sv) | 1979-08-17 |
| IT7820295A0 (it) | 1978-02-16 |
| AT373870B (de) | 1984-02-27 |
| JPS54130562A (en) | 1979-10-09 |
| MX5632E (es) | 1983-11-15 |
| GB2014990B (en) | 1982-06-09 |
| YU30879A (en) | 1983-02-28 |
| NL190845C (nl) | 1994-09-16 |
| YU41145B (en) | 1986-12-31 |
| DK152752C (da) | 1988-09-26 |
| NL7901251A (nl) | 1979-08-20 |
| ATA110179A (de) | 1983-07-15 |
| NL190845B (nl) | 1994-04-18 |
| CH639951A5 (de) | 1983-12-15 |
| GR78220B (xx) | 1984-09-26 |
| SE430888B (sv) | 1983-12-19 |
| FR2417498A1 (fr) | 1979-09-14 |
| GB2014990A (en) | 1979-09-05 |
| DK152752B (da) | 1988-05-09 |
| DK66579A (da) | 1979-08-17 |
| EG14440A (en) | 1984-03-31 |
| DE2903891C2 (xx) | 1992-02-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO2004011463A1 (en) | Modified pictet-spengler reaction and products prepared therefrom | |
| US4224239A (en) | Process for preparing optically active amino acid or mandelic acid | |
| JP2995704B2 (ja) | 光学活性な１ｈ−３−アミノピロリジン化合物の製造法 | |
| CA1097662A (en) | Process for preparing an optically active benzamide, the optically active benzamide so obtained, and pharmaceutical compositions containing it | |
| RU2730006C1 (ru) | Способ получения 5r-[(бензилокси)амино]пиперидин-2s-карбоновой кислоты или её производного | |
| US6197998B1 (en) | Process for producing N-glycyltyrosine and its crystal structure | |
| Allan et al. | Synthesis of analogues of GABA. III. All four stereoisomers of 3-aminocyclopentanecarboxylic acid and a stereochemical correlation with amidinomycin | |
| UA73472C2 (en) | A method for producing n-methyl-n-[(1s)-1-phenyl-2-((3s)-3-hydroxypyrrolidine-1-yl)ethyl]-2,2-diphenyl acetamide | |
| DE69821483T2 (de) | Verfahren zur gewinnung von chinaprylhydrochlorid und solvaten, die bei der isolierung und reinigung von chinaprylhydrochlorid nützlich sind | |
| CN109232254B (zh) | 一种化合物的合成方法及应用 | |
| US2762841A (en) | Process of producing l-glutamine | |
| CN111018692B (zh) | 以超强碱法制备1,2,3,4-四氢-1-萘甲酸的方法 | |
| CA1110639A (en) | Process for producing optically active bases | |
| CN111808040B (zh) | 多构型2-氧代噁唑烷-4-羧酸类化合物的合成方法 | |
| CN113105354B (zh) | 一种无催化剂制备n-(4-羟基-3-甲氧基苄基)壬酰胺的方法 | |
| US4511736A (en) | Process for the preparation of substituted chloroacetanilides | |
| US4804765A (en) | Process for synthesizing N-[(1'-allyl-2'pyrrolidinyl) methyl]2-methoxy-4,5-azimidobenzamide | |
| JP2947492B2 (ja) | テアニンの製造法 | |
| US3105852A (en) | Process for the preparation of l-(+)-glutamine | |
| SU543252A1 (ru) | Поизводные -замещенных имидов малеопимаровой кислоты, про вл ющие фунгицидную активность и способ их получени | |
| US3651137A (en) | Selective conversion of nalpha nepsilon-diacetyllysine esters to nalpha -diacetyllysine | |
| CN116496195A (zh) | 一种（r）-4,4-二氟代吡咯烷-2-羧酸的制备方法 | |
| Kajtár et al. | Synthesis and absolute configuration of three isomeric spiro-bis (2-pyrrolidinones) | |
| CH627742A5 (en) | Process for preparing 2-oxopyrrolidine derivatives | |
| JPS59155315A (ja) | イミダゾ−ル誘導体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |