JPS62255464A - Production of optically active cyanhydrin compound - Google Patents
Production of optically active cyanhydrin compoundInfo
- Publication number
- JPS62255464A JPS62255464A JP9921286A JP9921286A JPS62255464A JP S62255464 A JPS62255464 A JP S62255464A JP 9921286 A JP9921286 A JP 9921286A JP 9921286 A JP9921286 A JP 9921286A JP S62255464 A JPS62255464 A JP S62255464A
- Authority
- JP
- Japan
- Prior art keywords
- optically active
- formula
- compound
- dipeptide
- cyclo
- 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
- -1 cyanhydrin compound Chemical class 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 108010016626 Dipeptides Proteins 0.000 claims abstract description 11
- MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 125000000487 histidyl group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C([H])=N1 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 1
- 239000011261 inert gas Substances 0.000 abstract description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000013543 active substance Substances 0.000 abstract 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 230000000749 insecticidal effect Effects 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- HLXXMJDWTBXTOR-STQMWFEESA-N (3s,6s)-3-benzyl-6-(1h-imidazol-5-ylmethyl)piperazine-2,5-dione Chemical group C([C@@H]1NC([C@@H](NC1=O)CC=1NC=NC=1)=O)C1=CC=CC=C1 HLXXMJDWTBXTOR-STQMWFEESA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- HLXXMJDWTBXTOR-CHWSQXEVSA-N (3r,6r)-3-benzyl-6-(1h-imidazol-5-ylmethyl)piperazine-2,5-dione Chemical group C([C@H]1NC([C@H](NC1=O)CC=1N=CNC=1)=O)C1=CC=CC=C1 HLXXMJDWTBXTOR-CHWSQXEVSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
【発明の詳細な説明】
本発明は光学活性シアンヒドリン化合物の製造法１ζ関
し、さらに詳しくは、例えば殺虫性化合物などの生理活
性物質の合成中間体として有用な一般式（１）
〔式中、Ｒはアリール基、アルキル基またはシクロアル
キル基を表わし、黄は不斉炭素を表わす。〕
で示される光学活性シアンヒドリン化合物の製造法に関
する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method 1ζ for producing an optically active cyanohydrin compound, and more specifically, a compound of the general formula (1) [wherein R represents an aryl group, an alkyl group or a cycloalkyl group, and yellow represents an asymmetric carbon. ] It is related with the manufacturing method of the optically active cyanohydrin compound shown by these.
これまで合成ペプチドを触媒とする光学活性シアンヒド
リン化合物の製法としては、例えば本発明者らにより見
出された方法、即ちアルデヒド化合物および青酸（ＨＣ
Ｎ）とを例えばシクロｃ （Ｓ）−フェニルアラニル＝
（Ｓ）−ヒスチジル）ジペプチドなどの合成ペプチドの
存在下に反応させる方法が知られている（ Ｍ ａｋｒ
ｏｍｏ ｌ。Until now, as a method for producing an optically active cyanohydrin compound using a synthetic peptide as a catalyst, for example, the method discovered by the present inventors has been used.
N) and, for example, cyclo c (S)-phenylalanyl=
A method of reacting in the presence of synthetic peptides such as (S)-histidyl) dipeptide is known (Makr
omo l.
Ｃｈｅｍ、、１８０．１０８９（１９７９）、同１８３
，５７９（１９８２）、同１８６．１７５５（１９８５
）、Ｊ。Chem, 180.1089 (1979), 183
, 579 (1982), 186.1755 (1985)
), J.
Ｃｈｅｍ、 Ｓｏｃ、、Ｃｈｅｍ、 Ｃｏｍｍｕｎ、、
１９８１．２２９およびＢｕｌｌ、 Ｃｈｅｍ、 Ｓ
ｏｃ、 Ｊｐｎ−ｅ ５９．８９Ｂ（１９８６））。Chem、Soc、、Chem、Commun、、
1981.229 and Bull, Chem, S.
oc, Jpn-e 59.89B (1986)).
該方法は有用な光学活性なアルデヒド化合物が高い光学
収率で得られる方法として優れているものの、青酸を使
用することから種々の安全上の配慮を要し工業的製法と
しては必ずしも満足できるものではない。Although this method is excellent as a method for obtaining useful optically active aldehyde compounds in high optical yield, it requires various safety considerations due to the use of hydrocyanic acid, and is not necessarily satisfactory as an industrial production method. do not have.
このような状況の下に本発明者らはさらに検討を加えた
結果、アルデヒド化合物とアセトンシアノヒドリンとを
触媒としての光学活性な合成ジペプチドの存在下に反応
させることにより、容易に光学活性なシアノヒドリン化
合物が得られることを見出し本発明に至った。Under these circumstances, the present inventors conducted further studies and found that by reacting an aldehyde compound and acetone cyanohydrin in the presence of an optically active synthetic dipeptide as a catalyst, an optically active cyanohydrin compound can be easily produced. It was discovered that the following could be obtained, leading to the present invention.
即ち、本発明は、一般式（１）
％式％（１）
〔式中、Ｒは前述と同じ意味を有する。〕で示されるア
ルデヒド化合物とアセトンシアノヒドリンとを式（１）
〔式中、簀は前述と同じ意味を有する。〕で示されるシ
クロ（光学活性フェニルアラニル−光学活性−ヒスチジ
ル）ジペプチドの存在下に反応させることによる前記一
般式〔Ｉ警示される光学活性シアンヒドリン化合物の製
造法を提供するものである。That is, the present invention is based on the general formula (1) % formula % (1) [wherein R has the same meaning as described above]. The aldehyde compound represented by the formula (1) and the acetone cyanohydrin are represented by the formula (1) [wherein, 窀 has the same meaning as above. The present invention provides a method for producing an optically active cyanohydrin compound represented by the general formula [I] by reacting it in the presence of a cyclo(optically active phenylalanyl-optically active histidyl) dipeptide represented by the formula [I].
本発明方法によれば、青酸に比しその取り扱いが極めて
容易なアセトンシアノヒドリンを用い目的の光学活性シ
アンヒドリン化合物が効率よく得られることから殊に工
業的製造時に有利である。The method of the present invention is particularly advantageous in industrial production because the desired optically active cyanohydrin compound can be efficiently obtained using acetone cyanohydrin, which is much easier to handle than hydrocyanic acid.
以下に本発明方法につき説明する。The method of the present invention will be explained below.
本発明方法において、原料として用いられる一般式（１
）で示されるアルデヒド化合物の置換基ｌ＜とじては、
例えば、無置換、または低級アルキル基、低級アルコキ
シル基、ハロゲン原子、フェノキシ基、ハロゲン置換フ
ェノキシ基などのｆｆｆ換基含有しているフェニル基や
、低級アルキル基および炭素数４〜７のシクロアルキル
基などが挙げられる。In the method of the present invention, the general formula (1
) for the substituent l< of the aldehyde compound,
For example, phenyl groups that are unsubstituted or contain fff substituents such as lower alkyl groups, lower alkoxyl groups, halogen atoms, phenoxy groups, and halogen-substituted phenoxy groups, lower alkyl groups, and cycloalkyl groups having 4 to 7 carbon atoms. Examples include.
また、前記式（１）で示されるジペプチドとしては、シ
クロ（（Ｓ）−フェニルアラニル−（Ｓ）−ヒスチジル
）ジペプチドやシクロ（（Ｒ）−フェニルアラニル−（
Ｒ）−ヒスチジル）ジペプチドが挙げられる。Further, as the dipeptide represented by the formula (1), cyclo((S)-phenylalanyl-(S)-histidyl) dipeptide and cyclo((R)-phenylalanyl-(
R)-histidyl) dipeptide.
本発明方法において反応は通常ベンゼン、トルエンなど
の芳香族炭化水累、ヘキサン、ヘブクンなどの脂肪族炭
化水素、ジエチルエーテルなどのエーテル、ジクロルメ
タン、四塩化炭素などのハロゲン化炭化水素、アセトニ
トリルなどの不活性溶媒の存在下に行なわれる。In the method of the present invention, the reaction is usually carried out with aromatic hydrocarbons such as benzene and toluene, aliphatic hydrocarbons such as hexane and hebukun, ethers such as diethyl ether, halogenated hydrocarbons such as dichloromethane and carbon tetrachloride, and non-hydrocarbons such as acetonitrile. It is carried out in the presence of an active solvent.
また、反応温度は、−１０°Ｃ〜８０℃の範囲、通常は
０ ’Ｃ〜６０’Ｃで行なわれる。Further, the reaction temperature is in the range of -10°C to 80°C, usually 0'C to 60'C.
反応はアルゴン、ダ素などの不活性ガスの雰囲下に行な
・）ことが望ましい。使用されるアセトンシアノヒドリ
ンの量はアルデヒド化合物に対し当モル以上であれば特
に制限されるものではないが通常１〜２倍モルの量比で
用いられ、また、式（１）で示されるジペプチドの使用
量はアルデヒド化合物に対し、１／１００〜１／１０モ
ル程度の触媒量である。It is preferable that the reaction be carried out in an atmosphere of an inert gas such as argon or Da. The amount of acetone cyanohydrin used is not particularly limited as long as it is at least the equivalent molar amount to the aldehyde compound, but it is usually used at a molar ratio of 1 to 2 times. The amount used is a catalytic amount of about 1/100 to 1/10 mole based on the aldehyde compound.
反応終了後の反応液は、これに少量の鉱酸を添加した後
、濃縮、濾過などの通常の後処理、また必要に応じ、シ
リカゲルクロマトグラフィーなどの操作に処することに
より目的物を得ることができる。After the reaction is complete, the reaction solution can be subjected to normal post-treatments such as concentration and filtration after adding a small amount of mineral acid, and if necessary, can be subjected to operations such as silica gel chromatography to obtain the desired product. can.
以下に本発明を実施例でさらに詳細に説明する。The present invention will be explained in more detail below with reference to Examples.
実施例
シクロ（（Ｓ）−フェニルアラニル−（Ｓ） −ヒスチ
ジル）ジブチド１．０ミリモルを反応容器に入れ、容器
内を窒素ガスで置換した。次いでこれにベンゼン１０ｍ
１．アセトンシアノヒドリン２５ミリモルおよび下記表
に記載のアルデヒド化合物２５ミリモルを加え、５゜℃
で１時間撹拌した。Example 1.0 mmol of cyclo((S)-phenylalanyl-(S)-histidyl) dibutide was placed in a reaction vessel, and the inside of the vessel was purged with nitrogen gas. Next, add 10 m of benzene to this.
1. Add 25 mmol of acetone cyanohydrin and 25 mmol of the aldehyde compound listed in the table below, and heat to 5°C.
The mixture was stirred for 1 hour.
次に反応液に２Ｎ−塩酸−メタノール溶液０、５ ｔｔ
ｌを加えた後、減圧下に反応液を濃縮し、得られた残渣
にエーテルを加えた後、濾過１こより触媒を除去した。Next, add 0.5 tt of 2N-hydrochloric acid-methanol solution to the reaction solution.
1 was added, the reaction solution was concentrated under reduced pressure, ether was added to the resulting residue, and the catalyst was removed through filtration.
Ｐ液を減圧下に濃縮した後、残渣をシリカゲルカラムク
ロマトグラフィー（流下液：酢酸エチル）に付し、残存
するジペフチドを除去した。流出液を濃縮し、得られた
残渣につき、 Ｈ−ＮＭＲスペクトル（重クロロホルム
中）を測定し、δ１．６８ｐ１）ｍのピーク（未反応ア
セトンシアノヒドリンの−ＣＨ，） ）ｒよびδ４．１
〜４．５ｐｐｍのピーク（生成シアノヒドリン化合物の
一〇Ｈ（ＯＨ）ＣＮ）の比より転換率を求めた。After concentrating the P solution under reduced pressure, the residue was subjected to silica gel column chromatography (flowing liquid: ethyl acetate) to remove remaining dipeftide. The effluent was concentrated, and the resulting residue was subjected to H-NMR spectroscopy (in deuterated chloroform).
The conversion rate was determined from the ratio of the peak at ~4.5 ppm (10H(OH)CN of the cyanohydrin compound produced).
次いで、該残渣をさらに減圧下５０°Ｃで０縮し未反応
アセトンシアノヒドリンを留去し、夫々目的の光学活性
シアンヒドリン化合物を得た。Next, the residue was further subjected to zero condensation at 50°C under reduced pressure to distill off unreacted acetone cyanohydrin, thereby obtaining the desired optically active cyanohydrin compounds.
結果を下表に示す。The results are shown in the table below.
尚、上記各実施例において、シクロ（（Ｓ） −フヱニ
ルー（Ｓ）−ヒスチジル）ジペプチドに代えてシクロ（
（Ｒ）−フェニル−（Ｒ）−ヒスチジル）ジペプチドを
使用することにより（＋）／（−）比（（ｆ（） ／
（Ｓ）比）の逆転した組成の光学活性シアノヒドリン化
合物が得られる。In each of the above Examples, cyclo((S)-phenylated(S)-histidyl) dipeptide was replaced by cyclo(
By using (R)-phenyl-(R)-histidyl) dipeptide, the (+)/(-) ratio ((f()/
(S) ratio) is obtained.
Claims (1)
キル基を表わす。〕 で示されるアルデヒド化合物とアセトンシアノヒドリン
とをシクロ（光学活性フェニルアラニル−光学活性−ヒ
スチジル）ジペプチドの存在下に反応させることを特徴
とする一般式 ▲数式、化学式、表等があります▼ 〔式中、Ｒは前述と同じ意味を表わし、＊は不斉炭素を
表わす。〕 で示される光学活性シアンヒドリン化合物の製造法。[Claims] General formula [wherein R represents an aryl group, an alkyl group or a cycloalkyl group]. ] A general formula characterized by reacting an aldehyde compound represented by the formula with acetone cyanohydrin in the presence of a cyclo(optically active phenylalanyl-optically active histidyl) dipeptide ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [Formula In the formula, R has the same meaning as above, and * represents an asymmetric carbon. ] A method for producing an optically active cyanohydrin compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9921286A JPS62255464A (en) | 1986-04-28 | 1986-04-28 | Production of optically active cyanhydrin compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9921286A JPS62255464A (en) | 1986-04-28 | 1986-04-28 | Production of optically active cyanhydrin compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62255464A true JPS62255464A (en) | 1987-11-07 |
Family
ID=14241348
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9921286A Pending JPS62255464A (en) | 1986-04-28 | 1986-04-28 | Production of optically active cyanhydrin compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62255464A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59116256A (en) * | 1982-11-22 | 1984-07-05 | イー・アイ・デュ・ポン・ドゥ・ヌムール・アンド・カンパニー | Manufacture of optically active cyanomethyl ester |
-
1986
- 1986-04-28 JP JP9921286A patent/JPS62255464A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59116256A (en) * | 1982-11-22 | 1984-07-05 | イー・アイ・デュ・ポン・ドゥ・ヌムール・アンド・カンパニー | Manufacture of optically active cyanomethyl ester |
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