JPH0452265B2 - - Google Patents
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- Publication number
- JPH0452265B2 JPH0452265B2 JP915984A JP915984A JPH0452265B2 JP H0452265 B2 JPH0452265 B2 JP H0452265B2 JP 915984 A JP915984 A JP 915984A JP 915984 A JP915984 A JP 915984A JP H0452265 B2 JPH0452265 B2 JP H0452265B2
- Authority
- JP
- Japan
- Prior art keywords
- cis
- dicarboxylic acid
- acid
- formula
- water
- 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
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- QSMUFXXTSUEZJA-IYBDPMFKSA-N (4s,5r)-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid Chemical compound N1([C@@H]([C@@H](N(C1=O)CC=1C=CC=CC=1)C(=O)O)C(O)=O)CC1=CC=CC=C1 QSMUFXXTSUEZJA-IYBDPMFKSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 3
- LUMVCLJFHCTMCV-UHFFFAOYSA-M potassium;hydroxide;hydrate Chemical compound O.[OH-].[K+] LUMVCLJFHCTMCV-UHFFFAOYSA-M 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- XTMPFXTWTYPFSH-UHFFFAOYSA-N 2-oxoimidazolidine-4,5-dicarboxylic acid Chemical compound OC(=O)C1NC(=O)NC1C(O)=O XTMPFXTWTYPFSH-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- -1 alkyl chlorocarbonate Chemical compound 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 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
- 239000012530 fluid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Description
【発明の詳細な説明】
本発明は式〔〕
〔式中、Ｒはメチル、エチル等のC1-4低級アル
キル基を意味する。〕
で示されるシス−ジエステル体の新規かつ工業的
製造方法に関する。[Detailed Description of the Invention] The present invention is based on the formula [] [In the formula, R means a C 1-4 lower alkyl group such as methyl or ethyl. ] It is related with the novel and industrial manufacturing method of the cis-diester body shown by these.
更に詳しくは式〔〕
で示されるシス−ジカルボン酸を水溶液中ジアル
キシ硫酸と反応させることにより式〔〕で示さ
れるシス−ジエステル体を製造する方法に関す
る。 For more details, please refer to the formula [] The present invention relates to a method for producing a cis-diester represented by the formula [] by reacting a cis-dicarboxylic acid represented by the formula with dialxysulfuric acid in an aqueous solution.
本発明方法にて得ることができるシス−ジエス
テル体〔〕はビオチン等医薬品の合成中間体と
して有用なものである。（特開昭58−128376号公
報、同58−190395号公報）。 The cis-diester compound [] that can be obtained by the method of the present invention is useful as a synthetic intermediate for pharmaceuticals such as biotin. (Japanese Patent Application Laid-open No. 1983-128376, JP-A No. 58-190395).
従来シス−ジエステル体（）の製造方法とし
ては単離されたシス−ジカルボン酸体〔〕をル
イス酸の存在下メタノールと反応させて得るとい
う方法が知られていた〔J.Amer.Chem.，Soc.，
100(5) 1558−1563（1978）〕
本発明者らは上記エステル化反応では高価なル
イス酸を使用するということから、別途エステル
化反応を鋭意検討し、ルイス酸に代えて、硫酸を
用いると無水のシス−ジカルボン酸〔〕からシ
ス−ジエステル体〔〕が収率よく得られるとい
うことを見出し、本発明を完成した。 Conventionally, the method for producing the cis-diester compound () was known by reacting the isolated cis-dicarboxylic acid compound with methanol in the presence of a Lewis acid [J. Amer. Chem., Soc.，
100(5) 1558-1563 (1978)] Since the above-mentioned esterification reaction uses an expensive Lewis acid, the present inventors conducted a separate study on the esterification reaction and used sulfuric acid instead of the Lewis acid. The present invention was completed based on the discovery that a cis-diester compound [] can be obtained in good yield from anhydrous cis-dicarboxylic acid [].
以下に本発明方法を具体的に説明する。 The method of the present invention will be specifically explained below.
シス−ジカルボン酸〔〕を１〜20％含む水溶
液に、必要に応じ塩酸、硫酸、リン酸等の鉱酸、
あるいは炭酸ガス、又は水酸化ナトリウム、水酸
化カリウム、炭酸水素ナトリウム、炭酸水素カリ
ウム、炭酸ナトリウム、炭酸カリウム等の無機塩
基を加え、水溶液のPHを６〜10に調製した後、シ
ス−ジカルボン酸に対し２〜20倍モルのジメチル
硫酸等のジアルキル硫酸を加え反応させることに
よりシス−ジエステル体（）を得ることができ
る。反応温度としては−20°〜80℃、好ましくは
−10〜30℃にて実施することができ、反応中の反
応液のPHは６〜10に保つことが好ましい。 If necessary, add mineral acids such as hydrochloric acid, sulfuric acid, phosphoric acid, etc. to an aqueous solution containing 1 to 20% of cis-dicarboxylic acid.
Alternatively, add carbon dioxide gas or an inorganic base such as sodium hydroxide, potassium hydroxide, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, etc. to adjust the pH of the aqueous solution to 6 to 10, and then add cis-dicarboxylic acid. By adding 2 to 20 times the molar amount of dialkyl sulfuric acid such as dimethyl sulfuric acid to the reaction mixture, a cis-diester compound () can be obtained. The reaction temperature can be carried out at -20° to 80°C, preferably -10 to 30°C, and the pH of the reaction solution during the reaction is preferably maintained at 6 to 10.
反応液にトルエン、１，２−ジクロロエタン、
ジクロルメタン、アセトン、テトラヒドロフラン
等の有機溶媒を加えて同様の反応を行つても良
い。 Toluene, 1,2-dichloroethane,
A similar reaction may be carried out by adding an organic solvent such as dichloromethane, acetone, or tetrahydrofuran.
反応終了後、析出物を別することにより、シ
ス−ジエステル体（）を得ることができ、又、
通常の抽出操作を行うことによつてもシス−ジエ
ステル体（）を得ることもできる。 After the reaction is completed, the cis-diester compound () can be obtained by separating the precipitate, and
The cis-diester compound () can also be obtained by performing a normal extraction operation.
必要に応じ、上記方法で得られるシス−ジエス
テル体（）をメタノール、エタノール、アセト
ン等及びそれらの含水溶媒を用い精製すること、
及び／あるいは細かな結晶を得ることができる。 If necessary, purifying the cis-diester body () obtained by the above method using methanol, ethanol, acetone, etc. and their water-containing solvents,
and/or fine crystals can be obtained.
本発明方法の原料であるシス−ジカルボン酸
〔〕は工業的には、たとえば式〔〕
で示されるジカルボン酸を水溶液中アルカリ性条
件下ホスゲン（USP 2489232（1949））。あるいは
クロル炭酸アルキル（特開昭51−8270号公報）を
用いて反応することにより得られる。 The cis-dicarboxylic acid [] which is the raw material for the method of the present invention is industrially used, for example, with the formula [] The dicarboxylic acid represented by phosgene (USP 2489232 (1949)) under alkaline conditions in aqueous solution. Alternatively, it can be obtained by reacting with an alkyl chlorocarbonate (Japanese Unexamined Patent Publication No. 51-8270).
本発明本方法に従がえば、式〔〕で示される
ジカルボン酸から得られるシス−ジカルボン酸
（）を含む水溶液を原料として、そのまま用い
ジアルキル硫酸と反応させシス−ジエステル体
（）を収率良く得ることができ、必ずしもシス
−ジカルボン酸を単離して用いる必要はない。あ
るいは単離した場合に於ても乾燥が必要でない。
この点、本発明方法は工業上の製造における価値
の大きな方法である。 According to the method of the present invention, an aqueous solution containing a cis-dicarboxylic acid () obtained from a dicarboxylic acid represented by the formula [] is used as a raw material and reacted with dialkyl sulfuric acid to produce a cis-diester () in a high yield. It is not necessary to isolate and use the cis-dicarboxylic acid. Alternatively, even when isolated, drying is not necessary.
In this respect, the method of the present invention is of great value in industrial production.
（参考例）
シス−ジベンジルアミノコハク酸16.2gに10
％KOH水61g、トルエン105gを加え溶解した。
この溶液に25〜30℃にて35％KOH水でPHを10
〜11に調整しながらホスゲン17.1gを導入した。
反応液を分液し、シス−１，３−ジベンジル−
２−オキソイミダゾリジン−４，５−ジカルボ
ン酸を含む水溶液245gを得た。この水溶液は
下記条件下高速液体クロマトグラフイーで分析
し、シス−１，３−ジベンジル−２−オキソイ
ミダゾリジン−４，５−ジカルボン酸16.6gを
含有するものであつた。(Reference example) 10 to 16.2g of cis-dibenzylaminosuccinic acid
%KOH water (61 g) and toluene (105 g) were added and dissolved.
Bring this solution to pH 10 with 35% KOH water at 25-30℃.
17.1 g of phosgene was introduced while adjusting the temperature to ~11.
The reaction solution was separated into cis-1,3-dibenzyl-
245 g of an aqueous solution containing 2-oxoimidazolidine-4,5-dicarboxylic acid was obtained. This aqueous solution was analyzed by high performance liquid chromatography under the following conditions and was found to contain 16.6 g of cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid.
分析条件ム：μ−Bondapak C18（ウオターズ
社）
流動相：メタノール−水−AcOH（65
−35−１）
流 速：1.0ml／min
検 出：UV−254nm
参考例で得た水溶液100g（シス−１，３−
ジベンジル−２−オキソイミダゾリジン−４，
５−ジカルボン酸6.78gを含む）に水55ml、１，
２−ジクロルエタン40mlを加えたのち、濃塩酸
を滴下し、PH１とした。これを20〜25℃で６時
間攪拌した。析出結晶を反応液から別し、
１，２−ジクロルエタン100ml、水50mlで洗浄
後、乾燥し、結晶としてシス−１，３−ジベン
ジル−２−オキソイミダゾリジン−４，５−ジ
カルボン酸6.44gを得た。m.p.173−175℃
参考例で得たシス−１，３−ジベンジル−
２−オキソイミダゾリジン−４，５−ジカルボ
ン酸6.44gにメタノール39ml、濃硫酸3.27gを加
え、６時間還流した。この反応液を、重炭酸カ
リウム10.0g、水39mlの溶液中に滴下し、滴下
後20〜25℃で１時間攪拌した。 Analysis conditions: μ-Bondapak C 18 (Waters) Fluid phase: methanol-water-AcOH (65
-35-1) Flow rate: 1.0ml/min Detection: UV-254nm 100g of the aqueous solution obtained in the reference example (cis-1,3-
dibenzyl-2-oxoimidazolidine-4,
(containing 6.78 g of 5-dicarboxylic acid), 55 ml of water, 1,
After adding 40 ml of 2-dichloroethane, concentrated hydrochloric acid was added dropwise to adjust the pH to 1. This was stirred at 20-25°C for 6 hours. Separate the precipitated crystals from the reaction solution,
After washing with 100 ml of 1,2-dichloroethane and 50 ml of water, the mixture was dried to obtain 6.44 g of cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid as crystals. mp173−175℃ Cis-1,3-dibenzyl- obtained in reference example
39 ml of methanol and 3.27 g of concentrated sulfuric acid were added to 6.44 g of 2-oxoimidazolidine-4,5-dicarboxylic acid, and the mixture was refluxed for 6 hours. This reaction solution was dropped into a solution of 10.0 g of potassium bicarbonate and 39 ml of water, and after the dropwise addition, the mixture was stirred at 20 to 25°C for 1 hour.
析出した白色結晶を過、水洗浄後乾燥し、
シス−１，３−ジベンジル−２−オキソイミダ
ゾリジン−４，５−ジカルボン酸ジメチルエス
テル6.56gを得た。 The precipitated white crystals were filtered, washed with water, and dried.
6.56 g of cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid dimethyl ester was obtained.
m.p. 108−109℃
（実施例 １）
参考例で得たシス−１，３−ジベンジル−２
−オキソイミダゾリジン−４，５−ジカルボン酸
3.54gに２％KOH水58gを加え溶解した。この溶
液を濃塩酸にてPH9.0に調整し、これにジメチル
硫酸20.2gを加え15％NaOH水でPHを8.0〜9.0に調
整しながら25〜30℃で４時間攪拌した。反応液を
酢酸エチル100mlで抽出し、有機層を水洗浄後減
圧濃縮し、シス−１，３−ジベンジル−２−オキ
ソイミダゾリジン−４，５−ジカルボン酸ジメチ
ルエステル3.63g（収率95％）を得た。m.p.107−
109℃
（実施例 ２）
参考例で得た水溶液100g（シス−１，３−ジ
ベンジル−２−オキソイミダゾリジン−４，５−
ジカルボン酸6.78gを含む）に濃塩酸を滴下し、
PH9.5に調整した。 mp 108-109℃ (Example 1) Cis-1,3-dibenzyl-2 obtained in Reference Example
-oxoimidazolidine-4,5-dicarboxylic acid
58 g of 2% KOH water was added to 3.54 g and dissolved. This solution was adjusted to pH 9.0 with concentrated hydrochloric acid, 20.2 g of dimethyl sulfate was added thereto, and the solution was stirred at 25-30° C. for 4 hours while adjusting the pH to 8.0-9.0 with 15% NaOH water. The reaction solution was extracted with 100 ml of ethyl acetate, and the organic layer was washed with water and concentrated under reduced pressure to obtain 3.63 g of cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-dicarboxylic acid dimethyl ester (yield 95%). I got it. mp107−
109°C (Example 2) 100 g of the aqueous solution obtained in Reference Example (cis-1,3-dibenzyl-2-oxoimidazolidine-4,5-
(containing 6.78g of dicarboxylic acid), add concentrated hydrochloric acid dropwise,
Adjusted to PH9.5.
この反応液にジメチル硫酸33.7gを加え、15％
NaOH水でPHを8.0〜9.0に調整しながら25〜30℃
で４時間攪拌した。反応液を酢酸エチル150mlに
て抽出し、有機層を水洗浄後、減圧濃縮した。残
渣をメタノール70mlにて再結晶し、シス−１，３
−ジベンジル−２−オキソイミダゾリジン−４，
５−ジカルボン酸ジメチルエステル6.75gを得た。
m.p.109〜111℃ Add 33.7g of dimethyl sulfate to this reaction solution to make a 15%
25-30℃ while adjusting pH to 8.0-9.0 with NaOH water
The mixture was stirred for 4 hours. The reaction solution was extracted with 150 ml of ethyl acetate, and the organic layer was washed with water and concentrated under reduced pressure. The residue was recrystallized from 70 ml of methanol to give cis-1,3
-dibenzyl-2-oxoimidazolidine-4,
6.75 g of 5-dicarboxylic acid dimethyl ester was obtained.
mp109~111℃
Claims (1)
キル硫酸と反応させることを特徴とする式 〔式中、Ｒは低級アルキル基を意味する。〕 で示されるシス−ジエステル体の製造方法。[Claims] 1 formula A formula characterized by reacting a cis-dicarboxylic acid represented by with dialkyl sulfuric acid in an aqueous solution [In the formula, R means a lower alkyl group. ] A method for producing a cis-diester body shown in the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP915984A JPS60152469A (en) | 1984-01-21 | 1984-01-21 | Preparation of cis-diester derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP915984A JPS60152469A (en) | 1984-01-21 | 1984-01-21 | Preparation of cis-diester derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60152469A JPS60152469A (en) | 1985-08-10 |
| JPH0452265B2 true JPH0452265B2 (en) | 1992-08-21 |
Family
ID=11712835
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP915984A Granted JPS60152469A (en) | 1984-01-21 | 1984-01-21 | Preparation of cis-diester derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60152469A (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006232743A (en) * | 2005-02-25 | 2006-09-07 | Sumitomo Chemical Co Ltd | Method for producing dimethyl-1, 3-dibenzyl-2-oxo- imidazolidine-4, 5-dicarboxylate |
| CN105399677B (en) * | 2015-11-17 | 2019-02-22 | 蚌埠丰原医药科技发展有限公司 | A kind of preparation method of trans- naphthenic acid |
| CN106905239A (en) * | 2017-03-15 | 2017-06-30 | 安徽泰格维生素实业有限公司 | A kind of pair of process for purification of benzyl dicarboxylic acids |
-
1984
- 1984-01-21 JP JP915984A patent/JPS60152469A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60152469A (en) | 1985-08-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |