JPS6148819B2 - - Google Patents
Info
- Publication number
- JPS6148819B2 JPS6148819B2 JP4103082A JP4103082A JPS6148819B2 JP S6148819 B2 JPS6148819 B2 JP S6148819B2 JP 4103082 A JP4103082 A JP 4103082A JP 4103082 A JP4103082 A JP 4103082A JP S6148819 B2 JPS6148819 B2 JP S6148819B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- acid
- naphthyl
- methoxy
- chloroform
- 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims description 11
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 10
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
- 239000011707 mineral Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- -1 alkyl (6-methoxy-2-naphthyl)propionic acid Chemical compound 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
- 229910017604 nitric acid Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 46
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 15
- 230000003287 optical effect Effects 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 9
- 239000011259 mixed solution Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 description 1
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 description 1
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- XWJUDDGELKXYNO-QMMMGPOBSA-N desmethylnaproxen Chemical compound C1=C(O)C=CC2=CC([C@@H](C(O)=O)C)=CC=C21 XWJUDDGELKXYNO-QMMMGPOBSA-N 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960002009 naproxen Drugs 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4103082A JPS58157745A (ja) | 1982-03-16 | 1982-03-16 | ｄ−２−（６−メトキシ−２−ナフチル）プロピオン酸の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4103082A JPS58157745A (ja) | 1982-03-16 | 1982-03-16 | ｄ−２−（６−メトキシ−２−ナフチル）プロピオン酸の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58157745A JPS58157745A (ja) | 1983-09-19 |
| JPS6148819B2 true JPS6148819B2 (enrdf_load_stackoverflow) | 1986-10-25 |
Family
ID=12596994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4103082A Granted JPS58157745A (ja) | 1982-03-16 | 1982-03-16 | ｄ−２−（６−メトキシ−２−ナフチル）プロピオン酸の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58157745A (enrdf_load_stackoverflow) |
-
1982
- 1982-03-16 JP JP4103082A patent/JPS58157745A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58157745A (ja) | 1983-09-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2043649A1 (en) | Preparation of optically active aliphatic carboxylic acids | |
| JP2010248198A (ja) | （２ｒ）−２−プロピルオクタン酸の製造方法 | |
| US3733352A (en) | Preparation of d-threo-1-p-methyl-sulfonylphenyl-2-dichloro-acet-amidopropane-1,3-diol | |
| JPS6351136B2 (enrdf_load_stackoverflow) | ||
| FR2489312A1 (fr) | Procede pour la preparation de derives d'acides hydroxyphenyl aliphatiques et catalyseur utile a cet effet | |
| JP5001264B2 (ja) | アダマンタン誘導体の調製方法 | |
| JPS6148819B2 (enrdf_load_stackoverflow) | ||
| JPH11228512A (ja) | Ｄ−アロイソロイシンの製造方法および製造の中間体 | |
| EP0679629B1 (fr) | Procédé de préparation d'un acide alpha-(hydroxyphenoxy)-alcanecarboxylique optiquement actif et de ses dérivés | |
| JPH0641445B2 (ja) | 光学活性カルニチンエステルの製法 | |
| JPS581097B2 (ja) | 光学活性α−置換アリ−ル酢酸のラセミ化方法 | |
| KR920000953B1 (ko) | 광학활성 3, 4-디히드록시 부티르산 유도체의 제조방법 | |
| JPS61271261A (ja) | Ｌ−カルニチンの製法 | |
| JP2501852B2 (ja) | Ｓ−カルボキシメチル−ｌ−システインの製造法 | |
| AU776101B2 (en) | Production method of 2-cyclohexyl-2-hydroxy-2-phenylacetic acid intermediate therefor and production method thereof | |
| EP0000678B1 (fr) | Nouvel intermédiaire de synthèse: l'anthranilate de glycéryle et son procédé de préparation | |
| EP0419312A1 (fr) | Procédé de préparation d'acides aryl-2 propioniques optiquement actifs | |
| JPH0417938B2 (enrdf_load_stackoverflow) | ||
| GB2380996A (en) | Hydroxy-nitrobenzene derivatives useful in the preparation of formoterol | |
| JPH09278746A (ja) | 光学活性２−アラルキル−３−アシルチオプロピオン酸エステルの製造方法 | |
| JPH08510459A (ja) | （ｒ）−および（ｓ）−２−（４−アルカノイルフェノキシ）−プロピオン酸エステルの混合物または（ｒ）−および（ｓ）−２−（４−アロイルフェノキシ）−プロピオン酸エステルの混合物を製造する方法 | |
| JPS61212538A (ja) | α−アリ−ルアルカン酸エステル類の製造法 | |
| JP2002249461A (ja) | 高純度な酢酸化合物の製造方法及びそれによって得られた酢酸化合物 | |
| JP2001288138A (ja) | 含フッ素α，β−不飽和カルボン酸の製造方法 | |
| JPH0415787B2 (enrdf_load_stackoverflow) |