JPS596315B2 - 2-thienylsulfinyl acetic acid and its production method - Google Patents
2-thienylsulfinyl acetic acid and its production methodInfo
- Publication number
- JPS596315B2 JPS596315B2 JP15928976A JP15928976A JPS596315B2 JP S596315 B2 JPS596315 B2 JP S596315B2 JP 15928976 A JP15928976 A JP 15928976A JP 15928976 A JP15928976 A JP 15928976A JP S596315 B2 JPS596315 B2 JP S596315B2
- Authority
- JP
- Japan
- Prior art keywords
- acetic acid
- thienylsulfinyl
- production method
- acid
- dissolved
- 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
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は２−チエニルスルフイニル酢酸およびその光学
活性体ならびにその製造法に関するものである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to 2-thienylsulfinyl acetic acid, its optically active substance, and its production method.
２−チエニルスルフイニル酢酸は医薬等の中間体として
有用であり、特に（代）−２−チエニルスルフィニル酢
酸〔（代）は２−チエニルスルフイニル酢酸の光学異性
体のうちアルコール中の比旋光度ＣａＩＤが正を示すも
のと定義する。2-Thienylsulfinyl acetic acid is useful as an intermediate for pharmaceuticals, etc., and is particularly useful as an intermediate for pharmaceuticals, etc. It is defined that the optical rotation CaID is positive.
〕と７−アミノ−３−セフエム誘導体とを反応して得ら
れるセフアロスポリンは強い抗菌活性を示し、有用な物
質である。２−チエニルスルフイニル酢酸およびその光
学活性体は新規化合物である。] and a 7-amino-3-cephem derivative, cephalosporin is a useful substance that exhibits strong antibacterial activity. 2-Thienylsulfinyl acetic acid and its optically active form are new compounds.
２−チエニルスルフイニル酢酸は２−チエニルチオ酢酸
を酸化することによつて製造することができる。2-thienylsulfinylacetic acid can be produced by oxidizing 2-thienylthioacetic acid.
すなわち、２−チエニルチオ酢酸を酢酸に溶解し、氷冷
下で撹拌しつゝ、過酸化水素を加え、さらに室温で撹拌
した後、反応液から減圧下に酢酸を除き、残渣を酢酸エ
チルから再結晶すると２−チエニルスルフイニル酢酸が
得られる。（２）−２−チエニルスルフイニル酢酸はラ
セミ体の２−チエニルスルフイニル酢酸を光学分割する
ことによつて製造することができる。たとえば、ラセミ
２−チエニルスルフイニル酢酸ＩＯＶとブルリン２ ５
．７ｙを、２５０ゴのエタノールに溶解したのち濃縮載
置する。That is, 2-thienylthioacetic acid is dissolved in acetic acid, hydrogen peroxide is added while stirring under ice cooling, and after further stirring at room temperature, acetic acid is removed from the reaction solution under reduced pressure, and the residue is re-dissolved from ethyl acetate. When crystallized, 2-thienylsulfinyl acetic acid is obtained. (2)-2-Thienylsulfinyl acetic acid can be produced by optically resolving racemic 2-thienylsulfinyl acetic acid. For example, racemic 2-thienylsulfinyl acetic acid IOV and brulin 25
．． 7y was dissolved in 250 grams of ethanol and concentrated.
残渣の粉末を熱ベンゼンで洗滌したのち、不溶物２３．
５ｆ７をエタノール２００ｍｌから３回再結晶を繰返す
。得られる結晶Ｉｌｙを塩酸で処理し、酢酸エチルで抽
出し、有機層を濃縮して、さらに酢酸エチルから結晶化
させることにより、１．４Ｖの光学活性な２−チエニル
スルフイニル酢酸が得られる。比旋光度は＠■゜ ＋
３５、Ｏ゜（エタノール、Ｃ■１．０）であつた。実施
例
２−チエニルチオ酢酸８７Ｖを酢酸３０Ｏｍｌに溶解し
、氷冷下で撹拌しつゝ、３０％過酸化水素６８ｍｌを加
え、さらに室温で５時間撹拌する。After washing the residual powder with hot benzene, insoluble matter 23.
Repeat recrystallization of 5f7 from 200 ml of ethanol three times. By treating the resulting crystal Ily with hydrochloric acid, extracting with ethyl acetate, concentrating the organic layer, and further crystallizing from ethyl acetate, optically active 2-thienylsulfinyl acetic acid of 1.4 V is obtained. . Specific rotation is @■゜ +
The temperature was 35.0° (ethanol, C 1.0). Example 2 - 87V of thienylthioacetic acid is dissolved in 300ml of acetic acid, and while stirring under ice cooling, 68ml of 30% hydrogen peroxide is added, and the mixture is further stirred at room temperature for 5 hours.
Claims (1)
２−チエニルスルフイニル酢酸の製造法。[Claims] 1 1,2-thienylsulfinyl acetic acid. 2. A method for producing 2-thienylsulfinyl acetic acid, which comprises oxidizing 2-thienylthioacetic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15928976A JPS596315B2 (en) | 1976-12-29 | 1976-12-29 | 2-thienylsulfinyl acetic acid and its production method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15928976A JPS596315B2 (en) | 1976-12-29 | 1976-12-29 | 2-thienylsulfinyl acetic acid and its production method |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51007902A Division JPS5814440B2 (en) | 1976-01-29 | 1976-01-29 | Cephalosporins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52111562A JPS52111562A (en) | 1977-09-19 |
| JPS596315B2 true JPS596315B2 (en) | 1984-02-10 |
Family
ID=15690534
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15928976A Expired JPS596315B2 (en) | 1976-12-29 | 1976-12-29 | 2-thienylsulfinyl acetic acid and its production method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS596315B2 (en) |
-
1976
- 1976-12-29 JP JP15928976A patent/JPS596315B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52111562A (en) | 1977-09-19 |
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