JPH0242823B2 - - Google Patents
Info
- Publication number
- JPH0242823B2 JPH0242823B2 JP782583A JP782583A JPH0242823B2 JP H0242823 B2 JPH0242823 B2 JP H0242823B2 JP 782583 A JP782583 A JP 782583A JP 782583 A JP782583 A JP 782583A JP H0242823 B2 JPH0242823 B2 JP H0242823B2
- Authority
- JP
- Japan
- Prior art keywords
- trans
- acid
- carboxyethyl
- water
- hpa
- 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
- AUVZKHSBZVZBIU-HDJSIYSDSA-N C(#N)[C@@H]1CC[C@H](CC1)C(=O)OC1=CC=C(C=C1)CCC(=O)O Chemical compound C(#N)[C@@H]1CC[C@H](CC1)C(=O)OC1=CC=C(C=C1)CCC(=O)O AUVZKHSBZVZBIU-HDJSIYSDSA-N 0.000 claims description 6
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 2
- -1 phenyl trans-4-cyanocyclohexanecarboxylate Chemical compound 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- KJZWYCAIEUYAIW-UHFFFAOYSA-N 4-cyanocyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(C#N)CC1 KJZWYCAIEUYAIW-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XTNVLEVPXCVDTB-LJGSYFOKSA-N ClC(=O)[C@H]1CC[C@H](C#N)CC1 Chemical compound ClC(=O)[C@H]1CC[C@H](C#N)CC1 XTNVLEVPXCVDTB-LJGSYFOKSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- ZATPPBWCNUNFLZ-UHFFFAOYSA-N 4-carbamoylcyclohexane-1-carboxylic acid Chemical compound NC(=O)C1CCC(C(O)=O)CC1 ZATPPBWCNUNFLZ-UHFFFAOYSA-N 0.000 description 1
- XTNVLEVPXCVDTB-UHFFFAOYSA-N 4-cyanocyclohexane-1-carbonyl chloride Chemical compound ClC(=O)C1CCC(C#N)CC1 XTNVLEVPXCVDTB-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000000767 anti-ulcer Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- FHRSHSOEWXUORL-HDJSIYSDSA-N cetraxate Chemical compound C1C[C@@H](C[NH3+])CC[C@@H]1C(=O)OC1=CC=C(CCC([O-])=O)C=C1 FHRSHSOEWXUORL-HDJSIYSDSA-N 0.000 description 1
- USROQQUKEBHOFF-SKKCDYJJSA-N chembl502896 Chemical compound Cl.C1C[C@@H](CN)CC[C@@H]1C(=O)OC1=CC=C(CCC(O)=O)C=C1 USROQQUKEBHOFF-SKKCDYJJSA-N 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229940012957 plasmin Drugs 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は４−（２−カルボキシエチル）フエニ
ル トランス−４−シアノシクロヘキサンカルボ
キシラート（以下CNEと略称する）及びその製
造法に関する。
本発明の製造法は更に詳しくは式
（式中、Ｘはハロゲン原子を表わす）で表わさ
れる化合物を塩基の存在下４−ヒドロキシフエニ
ルプロピオン酸（以下HPAと略称する）と反応
させることからなるCNEの製造法である。
CNEは抗潰瘍作用及び抗プラスミン作用を有
する４−（２−カルボキシエチル）フエニル ト
ランス−４−アミノメチルシクロヘキサンカルボ
キシラート（以下NEと略称する）の合成中間体
として重要な化合物である。
本発明の製造法は、HPA及び塩基の水溶液に
式（）の化合物をそのまま又は有機溶媒に溶解
させた溶液として加えることにより実施される
が、式（）の化合物を製した際の反応液を
HPA及び塩基の水溶液に加えてもよく、この場
合には操作的に便利である。
HPA及び塩基の水溶液は、HPAもしくは
HPA及び塩基から製したHPAの塩及び塩基を水
に加えることにより製せられるが、水溶液中の塩
基がHPAに対し大過剰に存在すると生成した
CNEが加水分解されるので、水溶液中のHPAと
塩基の当量比が１：２〜３になるのが好ましい。
塩基としては、種々の無機塩基又は有機塩基の
使用が可能であり、例えば水酸化ナトリウム、水
酸化カリウム、水酸化カルシウム等のアルカリ金
属もしくはアルカリ土類金属の水酸化物又はトリ
エチルアミン、ピリジン等があげられる。
式（）の化合物及びHPAの使用量の割合は
通常等モル比でよいが、どちらかの化合物を過剰
に用いてもよい。
反応は０〜30℃で行うことが可能であるが、生
成物の加水分解を防ぐため０〜10℃で行うのが好
ましい。
有機溶媒としてはアルコール系、有機酸および
ケトン系以外のものが使用できるが、通常、塩化
メチレン、クロロホルム、四塩化炭素もしくは二
塩化エチレン等のハロゲン化炭化水素又はベンゼ
ンもしくはトルエン等の芳香族炭化水素が使用さ
れる。
反応系溶媒は水又は有機溶媒と水との混合溶媒
となるが、混合溶媒における水の割割合が少ない
とCNEの収率が低下するので、水の割合は70％
（容量）以上が好ましい。
反応終了後、反応液に酸を加えて酸性とし、次
いで溶媒を留去して反応液を濃縮すると結晶が析
出するので、これを濾取することにより高純度の
CNEを容易にかつ高純度で得ることができる。
得られたCNEはパラジウムもしくはニツケル
等の触媒の存在下接触還元することにより、医療
上有用なNEに導くことができる。
CNEを中間体として用いることによりNEを短
工程数で得ることができるので、本発明のCNE
はきわめて有用な化合物である。
次に実施例及び参考例を挙げて説明する。
実施例 １
トランス−４−シアノシクロヘキサンカルボン
酸16.8ｇをクロロホルム50ｇに溶解し、塩化チオ
ニル13.0ｇを加え１時間加熱還流する。クロロホ
ルムを減圧下留去し、トランス−４−シアノシク
ロヘキサンカルボン酸クロライドの結晶を得る。
この結晶を４−ヒドロキシフエニルプロピオン酸
16.6ｇ、トリエチルアミン20.2ｇ及び水166ｇの
溶液に撹拌10℃、30分間で添加する。添加後濃塩
酸でPH２とし、析出した結晶を濾取し、融点182
℃の４−（２−カルボキシエチル）フエニル ト
ランス−４−シアノシクロヘキサンカルボキシラ
ート27.1ｇ（収率90％）を得る。
元素分析値 C17H19NO4
計算値 Ｃ 67.76，Ｈ 6.35，Ｎ 4.65
実測値 Ｃ 67.68，Ｈ 6.23，Ｎ 4.55
IRνKBr nax（cm-1）：
2230（−CN），1740（
The present invention relates to 4-(2-carboxyethyl)phenyl trans-4-cyanocyclohexanecarboxylate (hereinafter abbreviated as CNE) and a method for producing the same. In more detail, the manufacturing method of the present invention is expressed by the formula This is a method for producing CNE, which comprises reacting a compound represented by the formula (wherein, X represents a halogen atom) with 4-hydroxyphenylpropionic acid (hereinafter abbreviated as HPA) in the presence of a base. CNE is an important compound as an intermediate for the synthesis of 4-(2-carboxyethyl)phenyl trans-4-aminomethylcyclohexanecarboxylate (hereinafter abbreviated as NE), which has anti-ulcer and anti-plasmin effects. The production method of the present invention is carried out by adding the compound of formula () as it is or as a solution dissolved in an organic solvent to an aqueous solution of HPA and a base.
It may also be added to an aqueous solution of HPA and base, in which case it is operationally convenient. The aqueous solution of HPA and base is
It is produced by adding a salt of HPA made from HPA and a base to water, but it is produced when the base in the aqueous solution is present in large excess relative to HPA.
Since CNE is hydrolyzed, the equivalent ratio of HPA to base in the aqueous solution is preferably 1:2 to 3. As the base, various inorganic or organic bases can be used, such as alkali metal or alkaline earth metal hydroxides such as sodium hydroxide, potassium hydroxide, calcium hydroxide, triethylamine, pyridine, etc. It will be done. The compound of formula () and HPA may be used in an equimolar ratio, but either compound may be used in excess. The reaction can be carried out at 0-30°C, but is preferably carried out at 0-10°C to prevent hydrolysis of the product. Organic solvents other than alcohols, organic acids and ketones can be used, but usually halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride or ethylene dichloride, or aromatic hydrocarbons such as benzene or toluene. is used. The reaction solvent will be water or a mixed solvent of organic solvent and water, but if the proportion of water in the mixed solvent is small, the yield of CNE will decrease, so the proportion of water should be 70%.
(capacity) or more is preferable. After the reaction is completed, acid is added to the reaction solution to make it acidic, and then the solvent is distilled off to concentrate the reaction solution, which precipitates crystals, which are collected by filtration to obtain high purity.
CNE can be obtained easily and with high purity. The obtained CNE can be converted into medically useful NE by catalytic reduction in the presence of a catalyst such as palladium or nickel. By using CNE as an intermediate, NE can be obtained in a short number of steps.
is an extremely useful compound. Next, examples and reference examples will be given and explained. Example 1 16.8 g of trans-4-cyanocyclohexanecarboxylic acid was dissolved in 50 g of chloroform, 13.0 g of thionyl chloride was added, and the mixture was heated under reflux for 1 hour. Chloroform was distilled off under reduced pressure to obtain crystals of trans-4-cyanocyclohexanecarboxylic acid chloride.
These crystals were converted into 4-hydroxyphenylpropionic acid.
16.6 g of triethylamine, 20.2 g of triethylamine, and 166 g of water with stirring at 10° C. for 30 minutes. After the addition, the pH was adjusted to 2 with concentrated hydrochloric acid, the precipitated crystals were collected by filtration, and the melting point was 182.
27.1 g (yield 90%) of 4-(2-carboxyethyl)phenyl trans-4-cyanocyclohexanecarboxylate at 0.degree. Elemental analysis value C 17 H 19 NO 4 Calculated value C 67.76, H 6.35, N 4.65 Actual value C 67.68, H 6.23, N 4.55 IRν KBr nax (cm -1 ): 2230 (-CN), 1740 (
【式】）
実施例 ２
トランス−４−シアノシクロヘキサンカルボン
酸16.8ｇをベンゼン50ｇに懸濁し塩化チオニル
13.0ｇを加え90℃で１時間撹拌し、トランス−４
−シアノシクロヘキサンカルボン酸クロライドと
する。反応液を４−ヒドロキシフエニルプロピオ
ン酸16.6ｇ、水酸化ナトリウム8.8ｇ及び水160ｇ
の溶液に撹拌下５℃、45分間で滴下する。滴下後
濃塩酸でPH２とし減圧下ベンゼンを留去し析出し
た結晶を濾取する。この結晶をアセトンより再結
晶し融点181.2℃の白色針状晶として４−（２−カ
ルボキシエチル）フエニル トランス−４−シア
ノシクロヘキサンカルボキシラート24.1ｇ（収率
80％）を得る。
実施例 ３
トランス−４−シアノシクロヘキサンカルボン
酸16.8ｇを四塩化炭素60ｇに懸濁し、塩化チオニ
ル13.0ｇを加え80℃で１時間撹拌し、トランス−
４−シアノシクロヘキサンカルボン酸クロライド
とする。反応液を４−ヒドロキシフエニルプロピ
オン酸16.6ｇ、水酸化カリウム12.3ｇ及び水150
ｇの溶液に撹拌下10℃、60分間で滴下する。以下
実施例２と同様の操作を行い融点181℃の４−（２
−カルボキシエチル）フエニル トランス−４−
シアノシクロヘキサンカルボキシラート27.6ｇ
（収率92％）を得る。
実施例 ４
トランス−４−カルバモイルシクロヘキサンン
カルボン酸18.8ｇを二塩化エチレン60ｇに懸濁
し、これに塩化チオニル26ｇを加え３時間加熱還
流しトランス−４−シアノシクロヘキサンカルボ
ン酸クロライドとする。反応液を４−ヒドロキシ
フエニルプロピオン酸16.6ｇ、水酸化カルシウム
8.14ｇ及び水160ｇの溶液に撹拌下５℃、60分間
で滴下する。以下実施例２と同様の操作を行い融
点180℃の４−（２−カルボキシエチル）フエニル
トランス−４−シアノシクロヘキサンカルボキ
シラート27.5ｇ（収率92％）を得る。
参考例
４−（２−カルボキシエチル）フエニル トラ
ンス−４−シアノシクロヘキサンカルボキシラー
ト3.01ｇを10％アンモニア水3.5ml及び水27mlの
混液に溶解し、これにラネーニツケル１mlを加
え、常温、常圧下の水素気流中で５時間接触還元
する。還元液を濃塩酸でPH３に調整し、ラネーニ
ツケルを濾去する。濾液を減圧下40℃で10mlまで
濃縮し、冷却する。析出した結晶を濾取し水洗す
ると融点232℃の４−（２−カルボキシエチル）フ
エニル トランス−４−アミノメチルシクロヘキ
サンカルボキシラート・塩酸塩2.72ｇ（収率80
％）が得られる。[Formula]) Example 2 16.8 g of trans-4-cyanocyclohexanecarboxylic acid was suspended in 50 g of benzene and thionyl chloride was added.
Add 13.0g of trans-4 and stir at 90℃ for 1 hour.
-cyanocyclohexanecarboxylic acid chloride. The reaction solution was mixed with 16.6 g of 4-hydroxyphenylpropionic acid, 8.8 g of sodium hydroxide, and 160 g of water.
Add dropwise to the solution under stirring at 5°C for 45 minutes. After the addition, the pH was adjusted to 2 with concentrated hydrochloric acid, and benzene was distilled off under reduced pressure, and the precipitated crystals were collected by filtration. These crystals were recrystallized from acetone to give 24.1 g of 4-(2-carboxyethyl)phenyl trans-4-cyanocyclohexanecarboxylate as white needle-like crystals with a melting point of 181.2°C (yield:
80%). Example 3 16.8 g of trans-4-cyanocyclohexanecarboxylic acid was suspended in 60 g of carbon tetrachloride, 13.0 g of thionyl chloride was added, and the mixture was stirred at 80°C for 1 hour.
4-cyanocyclohexanecarboxylic acid chloride. The reaction solution was mixed with 16.6 g of 4-hydroxyphenylpropionic acid, 12.3 g of potassium hydroxide, and 150 g of water.
Add dropwise to the solution of g at 10°C for 60 minutes while stirring. Hereinafter, the same operation as in Example 2 was carried out to obtain 4-(2) with a melting point of 181°C.
-carboxyethyl)phenyl trans-4-
Cyanocyclohexanecarboxylate 27.6g
(yield 92%). Example 4 18.8 g of trans-4-carbamoylcyclohexanecarboxylic acid was suspended in 60 g of ethylene dichloride, and 26 g of thionyl chloride was added thereto, followed by heating under reflux for 3 hours to obtain trans-4-cyanocyclohexanecarboxylic acid chloride. Add 16.6 g of 4-hydroxyphenylpropionic acid and calcium hydroxide to the reaction solution.
Add dropwise to a solution of 8.14g and 160g of water at 5°C for 60 minutes while stirring. Thereafter, the same operation as in Example 2 was carried out to obtain 27.5 g (yield: 92%) of 4-(2-carboxyethyl)phenyl trans-4-cyanocyclohexanecarboxylate having a melting point of 180°C. Reference Example 3.01 g of 4-(2-carboxyethyl)phenyl trans-4-cyanocyclohexanecarboxylate was dissolved in a mixture of 3.5 ml of 10% aqueous ammonia and 27 ml of water, 1 ml of Raney Nickel was added thereto, and hydrogenated at room temperature and pressure. Catalytic reduction for 5 hours in a stream of air. The reduced solution is adjusted to pH 3 with concentrated hydrochloric acid, and Raney nickel is removed by filtration. The filtrate is concentrated to 10 ml under reduced pressure at 40°C and cooled. The precipitated crystals were collected by filtration and washed with water to give 2.72 g of 4-(2-carboxyethyl)phenyl trans-4-aminomethylcyclohexanecarboxylate hydrochloride with a melting point of 232°C (yield: 80
%) is obtained.
Claims (1)
トランス−４−シアノシクロヘキサンカルボ
キシラート ２ 式 （式中、Ｘはハロゲン原子を表わす）で表わさ
れる化合物を塩基の存在下４−ヒドロキシフエニ
ルプロピオン酸と反応させることを特徴とする４
−（２−カルボキシエチル）フエニル トランス
−４−シアノシクロヘキサンカルボキシラートの
製造法。[Claims] 1 1 4-(2-carboxyethyl)phenyl trans-4-cyanocyclohexanecarboxylate 2 Formula (wherein, X represents a halogen atom) is reacted with 4-hydroxyphenylpropionic acid in the presence of a base.
A method for producing -(2-carboxyethyl)phenyl trans-4-cyanocyclohexanecarboxylate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP782583A JPS59134766A (en) | 1983-01-20 | 1983-01-20 | Cyanocyclohexanecarboxylate and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP782583A JPS59134766A (en) | 1983-01-20 | 1983-01-20 | Cyanocyclohexanecarboxylate and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59134766A JPS59134766A (en) | 1984-08-02 |
| JPH0242823B2 true JPH0242823B2 (en) | 1990-09-26 |
Family
ID=11676368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP782583A Granted JPS59134766A (en) | 1983-01-20 | 1983-01-20 | Cyanocyclohexanecarboxylate and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59134766A (en) |
-
1983
- 1983-01-20 JP JP782583A patent/JPS59134766A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59134766A (en) | 1984-08-02 |
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