JP2002348282A - Method for producing 1,3-thiazolidine-4-carboxylic acid amide - Google Patents
Method for producing 1,3-thiazolidine-4-carboxylic acid amideInfo
- Publication number
- JP2002348282A JP2002348282A JP2001158362A JP2001158362A JP2002348282A JP 2002348282 A JP2002348282 A JP 2002348282A JP 2001158362 A JP2001158362 A JP 2001158362A JP 2001158362 A JP2001158362 A JP 2001158362A JP 2002348282 A JP2002348282 A JP 2002348282A
- Authority
- JP
- Japan
- Prior art keywords
- thiazolidine
- carboxylic acid
- acid amide
- producing
- amide
- 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.)
- Pending
Links
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
Abstract
(57)【要約】
【課題】 各種工業薬品、農薬、および医薬品の製造中
間体として有用な１，３−チアゾリジン−４−カルボン
酸アミドを製造する実用的な方法を提供する。
【解決手段】 ペニシラミンアミドを代表とする特定の
構造を有するアミドとアセトンとを、水を溶媒とし、反
応温度１０〜６０℃にて反応させて１，３−チアゾリジ
ン−４−カルボン酸アミドを生成せしめる。この際触媒
を用いなくとも十分な反応速度が得られる。PROBLEM TO BE SOLVED: To provide a practical method for producing 1,3-thiazolidine-4-carboxylic acid amide useful as an intermediate for producing various industrial chemicals, agricultural chemicals and pharmaceuticals. SOLUTION: An amide having a specific structure represented by penicillamine amide is reacted with acetone at a reaction temperature of 10 to 60 ° C using water as a solvent to produce 1,3-thiazolidine-4-carboxylic acid amide. Let me know. In this case, a sufficient reaction rate can be obtained without using a catalyst.
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、一般式（２）で示
される１，３−チアゾリジン−４−カルボン酸アミドの
製造法に関する。１，３−チアゾリジン−４−カルボン
酸アミドは、生化学的に不斉加水分解して対応する光学
活性（４Ｒ）−１，３−チアゾリジン−４−カルボン酸
を製造する原料であり、各種工業薬品、農薬、および医
薬品の製造中間体として重要な物質である。The present invention relates to a method for producing 1,3-thiazolidine-4-carboxylic acid amide represented by the general formula (2). 1,3-Thiazolidine-4-carboxylic acid amide is a raw material for producing the corresponding optically active (4R) -1,3-thiazolidine-4-carboxylic acid by biochemically asymmetric hydrolysis. It is an important substance as an intermediate in the production of drugs, pesticides, and pharmaceuticals.
【０００２】[0002]
【従来の技術】一般式（１）で示されるアミドから一般
式（２）で示される１，３−チアゾリジン−４−カルボ
ン酸アミドを製造する方法は報告されていない。2. Description of the Related Art There has been no report on a method for producing a 1,3-thiazolidine-4-carboxylic acid amide represented by the general formula (2) from an amide represented by the general formula (1).
【０００３】[0003]
【発明が解決しようとする課題】本発明の目的は、光学
活性（４Ｒ）−１，３−チアゾリジン−４−カルボン酸
の製造原料で、各種工業薬品、農薬及び医薬品の製造中
間体として非常に重要な１，３−チアゾリジン−４−カ
ルボン酸アミドの製造法を提供することにある。An object of the present invention is to provide a raw material for producing optically active (4R) -1,3-thiazolidine-4-carboxylic acid, which is very useful as an intermediate for producing various industrial chemicals, agricultural chemicals and pharmaceuticals. It is an object of the present invention to provide a method for producing an important 1,3-thiazolidine-4-carboxylic acid amide.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、光学活性
（４Ｒ）−１，３−チアゾリジン−４−カルボン酸の製
造原料である１，３−チアゾリジン−４−カルボン酸ア
ミドの製造法に関して鋭意検討を行った結果、一般式が
（１）で示されるアミドとアセトンを反応させて一般式
（２）で示される１，３−チアゾリジン−４−カルボン
酸アミドを製造する本発明に到達した。即ち、本発明は
一般式が（１）で示されるアミドとアセトンを反応させ
て一般式（２）で示される１，３−チアゾリジン−４−
カルボン酸アミドを生成せしめることを特徴とする、
１，３−チアゾリジン−４−カルボン酸アミドの製造方
法に関する。Means for Solving the Problems The present inventors have prepared a method for producing 1,3-thiazolidine-4-carboxylic acid amide, which is a raw material for producing optically active (4R) -1,3-thiazolidine-4-carboxylic acid. As a result of intensive studies, the present invention reaches the present invention in which an amide represented by the general formula (1) is reacted with acetone to produce 1,3-thiazolidine-4-carboxylic acid amide represented by the general formula (2). did. That is, the present invention comprises reacting an amide represented by the general formula (1) with acetone to form a 1,3-thiazolidine-4- compound represented by the general formula (2).
Characterized by producing a carboxylic acid amide,
The present invention relates to a method for producing 1,3-thiazolidine-4-carboxylic acid amide.
【０００５】[0005]
【発明の実施の形態】以下に本発明の詳細について説明
する。前記の一般式（１）で示されるアミドのＲ1 ，Ｒ
2 は水素または低級アルキル基であればよく、特に制限
はないが、メチル基である場合が好適である。本発明の
一般式（１）で示されるアミドの代表例として、ペニシ
ラミンアミドなどがある。本発明の原料である一般式
（１）で示されるアミドは、その製法および品質等に特
に制限はなく、例えば特公昭５４−４９３６号公報記載
の方法で容易に得ることができる。DESCRIPTION OF THE PREFERRED EMBODIMENTS The details of the present invention will be described below. R 1 and R of the amide represented by the above general formula (1)
2 may be hydrogen or a lower alkyl group, and is not particularly limited, but is preferably a methyl group. Representative examples of the amide represented by the general formula (1) of the present invention include penicillamine amide. The amide represented by the general formula (1), which is a raw material of the present invention, is not particularly limited in its production method and quality, and can be easily obtained, for example, by the method described in JP-B-54-4936.
【０００６】本反応に使用する溶媒は特に制限はなく、
水が好的である。本反応においては別途触媒を加えなく
ても十分な反応速度が得られるので特に加える必要はな
い。原料のアミドとアセトンとの比率は、原料アミド１
モルに対してアセトン１〜１０モルの範囲とすることが
望ましい。反応温度１０〜６０℃、好適には２０〜４０
℃である。反応時間は反応温度により異なるが、通常
０．５〜２時間である。反応で生成した１，３−チアゾ
リジン−４−カルボン酸アミドは、反応終了後、常法に
より、例えば水と余剰アセトンを留去することで得るこ
とができる。以下、本発明を実施例によってさらに具体
的に説明するが、本発明はこれらの実施例に限定される
ものではない。The solvent used in this reaction is not particularly limited.
Water is favorable. In this reaction, a sufficient reaction rate can be obtained without separately adding a catalyst, so that it is not particularly necessary to add. The ratio of the raw material amide to acetone is the raw material amide 1
It is desirable that the amount be in the range of 1 to 10 mol of acetone based on the mol. Reaction temperature 10-60 ° C, preferably 20-40
° C. The reaction time varies depending on the reaction temperature, but is usually 0.5 to 2 hours. The 1,3-thiazolidine-4-carboxylic acid amide produced by the reaction can be obtained by, for example, distilling off water and excess acetone by a conventional method after completion of the reaction. Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples.
【０００７】[0007]
【実施例】実施例１ ２，２−ジメチル−５，５−ジメチル−１，６−チアゾ
リジン−４−カルボン酸アミドの製造 ペニシラミンアミド７４．０ｇ（０．５ｍｏｌ）を蒸留
水８００ｍｌに溶解させ、アセトン５８ｇ（１ｍｏｌ）
を加えた。常圧、撹拌下３０℃で１時間の反応後、冷却
した。次にエバポレーターで水、アセトンを留去した。
残渣をアセトンで洗浄し、２，２−ジメチル−５，５−
ジメチル−１，３−チアゾリジン−４−カルボン酸アミ
ドの白色結晶８６．５ｇ（０．４６ｍｏｌ）を得た。ペ
ニシラミンアミドに対する収率は９２モル％であった。Example 1 Preparation of 2,2-dimethyl-5,5-dimethyl-1,6-thiazolidine-4-carboxylic acid amide 74.0 g (0.5 mol) of penicillamine amide was dissolved in 800 ml of distilled water. Acetone 58g (1mol)
Was added. After reaction at 30 ° C. for 1 hour under stirring under normal pressure, the mixture was cooled. Next, water and acetone were distilled off by an evaporator.
The residue was washed with acetone and 2,2-dimethyl-5,5-
86.5 g (0.46 mol) of white crystals of dimethyl-1,3-thiazolidine-4-carboxylic acid amide were obtained. The yield based on penicillamine amide was 92 mol%.
【０００８】実施例２ ２，２−ジメチル−５，５−ジメチル−１，３−チアゾ
リジン−４−カルボン酸アミドの製造 ペニシラミンアミド７４．０ｇ（０．５ｍｏｌ）を蒸留
水８００ｍｌに溶解させ、アセトン１１８ｇ（２ｍｏ
ｌ）を加えた。常圧、撹拌下３０℃で１時間の反応後、
冷却した。次にエバポレーターで水、アセトンを留去し
た。残渣をアセトンで洗浄し、２，２−ジメチル−５，
５−ジメチル−１，３−チアゾリジン−４−カルボン酸
アミドの白色結晶９０．２ｇ（０．４８ｍｏｌ）を得
た。ペニシラミンアミドに対する収率は９６モル％であ
った。Example 2 Preparation of 2,2-dimethyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid amide 74.0 g (0.5 mol) of penicillamine amide was dissolved in 800 ml of distilled water, and acetone was dissolved. 118g (2mo
l) was added. After reaction at 30 ° C. for 1 hour under normal pressure and stirring,
Cool. Next, water and acetone were distilled off by an evaporator. The residue was washed with acetone and 2,2-dimethyl-5,
90.2 g (0.48 mol) of white crystals of 5-dimethyl-1,3-thiazolidine-4-carboxylic acid amide were obtained. The yield based on penicillamine amide was 96 mol%.
【０００９】[0009]
【発明の効果】各種工業薬品、農薬、および医薬品の製
造中間体として非常に有用な１，３−チアゾリジン−４
−カルボン酸アミドを製造することができる。EFFECT OF THE INVENTION 1,3-Thiazolidine-4 which is very useful as an intermediate for the production of various industrial chemicals, agricultural chemicals and pharmaceuticals
Carboxylic acid amides can be produced.
Claims (1)
トンを反応させて一般式（２）で示される１，３−チア
ゾリジン−４−カルボン酸アミドを生成せしめることを
特徴とする、１，３−チアゾリジン−４−カルボン酸ア
ミドの製造方法。ただし、一般式（１）及び（２）中の
Ｒ1 ，Ｒ2 は水素または炭素数１〜４の低級アルキル基
である。 【化１】 【化２】 An amide represented by the general formula (1) is reacted with acetone to produce a 1,3-thiazolidine-4-carboxylic acid amide represented by the general formula (2). For producing 3,3-thiazolidine-4-carboxylic acid amide. However, R 1 and R 2 in the general formulas (1) and (2) are hydrogen or a lower alkyl group having 1 to 4 carbon atoms. Embedded image Embedded image
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001158362A JP2002348282A (en) | 2001-05-28 | 2001-05-28 | Method for producing 1,3-thiazolidine-4-carboxylic acid amide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001158362A JP2002348282A (en) | 2001-05-28 | 2001-05-28 | Method for producing 1,3-thiazolidine-4-carboxylic acid amide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2002348282A true JP2002348282A (en) | 2002-12-04 |
Family
ID=19002099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001158362A Pending JP2002348282A (en) | 2001-05-28 | 2001-05-28 | Method for producing 1,3-thiazolidine-4-carboxylic acid amide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2002348282A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2005049557A1 (en) * | 2003-11-18 | 2007-06-07 | 三菱瓦斯化学株式会社 | Process for producing optically active 2-alkylcysteine, its derivative and process |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54106488A (en) * | 1978-02-04 | 1979-08-21 | Taisho Pharmaceut Co Ltd | Purification for d-penicillamine |
-
2001
- 2001-05-28 JP JP2001158362A patent/JP2002348282A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54106488A (en) * | 1978-02-04 | 1979-08-21 | Taisho Pharmaceut Co Ltd | Purification for d-penicillamine |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2005049557A1 (en) * | 2003-11-18 | 2007-06-07 | 三菱瓦斯化学株式会社 | Process for producing optically active 2-alkylcysteine, its derivative and process |
| EP1686114A4 (en) * | 2003-11-18 | 2007-08-15 | Mitsubishi Gas Chemical Co | Process for producing optically active 2-alkylcysteine, derivative thereof, and processes for production |
| US7470525B2 (en) | 2003-11-18 | 2008-12-30 | Mitsubishi Gas Chemical Company, Inc. | Process for producing optically active 2-alkycysteine, derivative thereof, and processes for production |
| JP4735263B2 (en) * | 2003-11-18 | 2011-07-27 | 三菱瓦斯化学株式会社 | Process for producing optically active 2-alkylcysteine, its derivative and process |
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