JPS62205065A - Production of oxazolone compound - Google Patents
Production of oxazolone compoundInfo
- Publication number
- JPS62205065A JPS62205065A JP4704786A JP4704786A JPS62205065A JP S62205065 A JPS62205065 A JP S62205065A JP 4704786 A JP4704786 A JP 4704786A JP 4704786 A JP4704786 A JP 4704786A JP S62205065 A JPS62205065 A JP S62205065A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- acid ester
- carbamic acid
- fluorine ion
- 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 oxazolone compound Chemical class 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical group 0.000 claims abstract description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 abstract description 21
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 abstract description 5
- 239000011737 fluorine Substances 0.000 abstract description 5
- 150000001336 alkenes Chemical class 0.000 abstract description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 3
- 238000007363 ring formation reaction Methods 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 abstract 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000000926 separation method Methods 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
- 239000000047 product Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- KFSZGBHNIHLIAA-UHFFFAOYSA-M benzyl(trimethyl)azanium;fluoride Chemical compound [F-].C[N+](C)(C)CC1=CC=CC=C1 KFSZGBHNIHLIAA-UHFFFAOYSA-M 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- MOVBJUGHBJJKOW-UHFFFAOYSA-N methyl 2-amino-5-methoxybenzoate Chemical compound COC(=O)C1=CC(OC)=CC=C1N MOVBJUGHBJJKOW-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、医薬品や農薬を製造するために用いる中間体
として有用なオキサシロン化合物の製造方法に関するも
のである。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for producing oxacilone compounds useful as intermediates used for producing pharmaceuticals and agricultural chemicals.
２ （３Ｈ）−オキサシロン化合物は、従来下記の化合
物Ａ、Ｂ、Ｃを用いて合成されている。2 (3H)-Oxacylone compounds have conventionally been synthesized using the following compounds A, B, and C.
しかしながら、上記のようにいずれの化合物を用いても
反応を多段階で行なわなけれならず、置換基も限られて
おり反応条件も過酷であって、経済的でないという問題
がある。さらにこれらの方法には収率も良好でないとい
う問題がある。However, as mentioned above, no matter which compound is used, the reaction must be carried out in multiple stages, the number of substituents is limited, the reaction conditions are harsh, and there are problems in that it is not economical. Furthermore, these methods have the problem of poor yields.
従って、本発明は、簡易な手段を用いて高収率でオキサ
シロン化合物を製造できる製造方法を提供することを目
的とする。Therefore, an object of the present invention is to provide a manufacturing method that can produce oxacilone compounds in high yield using simple means.
本発明は、カルバミン酸エステルを出発物質とし、フッ
素アニオンの塩基性を選択的に利用することにより、非
常に温和な条件で、オレフィンの生成と環化反応が進行
し、２ （３Ｈ）−オキサシロン化合物を収率よく合成
できるとの知見に基づいてなされたのである。すなわち
、本発明は、一般式（１）：
％式％（１）
（式中、Ｒ１は炭化水素基を示し、Ｘはハロゲンを示す
。）
で表わされるカルバミン酸エステルを、フッ素イオンの
存在下でオレフィンの生成と同時に環化させることを特
徴とす・る一般式（■）：ξ
（式中、Ｒ，及びＸは式（１）と同じ意味を有する。）
で表わされるオキサシロン化合物の製造方法。The present invention uses a carbamate ester as a starting material and selectively utilizes the basicity of the fluorine anion to proceed the production of olefin and the cyclization reaction under very mild conditions. This was done based on the knowledge that the compound could be synthesized with high yield. That is, the present invention provides a method for treating a carbamate ester represented by the general formula (1): % formula % (1) (wherein R1 represents a hydrocarbon group and X represents a halogen) in the presence of fluorine ions. Production of an oxacylone compound represented by the general formula (■): ξ (wherein R and Method.
本発明の製造方法において出発原料として使用するカル
バミン酸エステルは、例えば１．３−ジハロ−２−プロ
パツールとイソシアネートとカラ容易に製造される。本
発明では、一般式（１）で表わされる化合物のうち、一
般式（Ｉ）巾のＲＩがフェニル基、ナフチル基、アルキ
ル基、置換基（ハロゲンなど）を有するこれらの基であ
るものを用いるのが好ましい。又式中、Ｘのハロゲンと
しては、塩素又は臭素が好ましく、式中の２つのＸがと
もに塩素及び／又は臭素である。The carbamate ester used as a starting material in the production method of the present invention is easily produced from, for example, 1,3-dihalo-2-propatol and isocyanate. In the present invention, among the compounds represented by the general formula (1), those whose RI of the general formula (I) width is a phenyl group, a naphthyl group, an alkyl group, or any of these groups having a substituent (such as a halogen) are used. is preferable. In the formula, the halogen of X is preferably chlorine or bromine, and both X's in the formula are chlorine and/or bromine.
本発明では、上記カルバミン酸エステルをフッ素イオン
の存在下で環化させることを特徴とするが、フッ素イオ
ンを提供する化合物としては、フッ素アニオンを放出す
る任意の化合物が用いられる。これらの化合物のうち、
第４級アンモニウムフルオリド、特に一般式（■）：
（式中、Ｒ２〜Ｒ５は、炭素数１〜１６のアルキル基、
アルケニル基又は芳香族基を示す。）で表わされる第４
級アンモニウム塩を用いるのが好ましい。上記式（ＩＩ
Ｉ）において、Ｒ２〜Ｒ３は同一でも異なっていてもよ
く、特にＲ２〜Ｒ５は炭素数１〜１６のアルキル基が好
ましい。式中芳香族基としてはフェニル基、ベンジル基
などが好ましい。上記第４級アンモニウム塩として、具
体的には、テトラ（ｎ−ブチル）アンモニウムフロリド
（以下、ＴＢＡＦという）、テトラエチルアンモニウム
フルオリド、テトラメチルアンモニウムフルオリド、ベ
ンジルトリメチルアンモニウムフルオリドが例示される
。The present invention is characterized in that the above-mentioned carbamate ester is cyclized in the presence of fluorine ions, and any compound that releases fluorine anions can be used as the compound that provides fluorine ions. Of these compounds,
Quaternary ammonium fluoride, especially general formula (■): (wherein R2 to R5 are alkyl groups having 1 to 16 carbon atoms,
Indicates an alkenyl group or an aromatic group. )
Preferably, grade ammonium salts are used. The above formula (II
In I), R2 to R3 may be the same or different, and R2 to R5 are preferably alkyl groups having 1 to 16 carbon atoms. In the formula, the aromatic group is preferably a phenyl group, a benzyl group, or the like. Specific examples of the quaternary ammonium salt include tetra(n-butyl)ammonium fluoride (hereinafter referred to as TBAF), tetraethylammonium fluoride, tetramethylammonium fluoride, and benzyltrimethylammonium fluoride.
本発明では、上記第４級アンモニウム塩を、カルバミン
酸エステルに対して、２．２〜１０当量、好ましくは１
〜５当量の割合で存在させ、０℃〜５０℃の温度に２〜
２４時間加熱して下記の環化反応を行なうのである。In the present invention, the quaternary ammonium salt is used in an amount of 2.2 to 10 equivalents, preferably 1 equivalent to the carbamate ester.
~5 equivalents and at a temperature of 0°C to 50°C.
The following cyclization reaction is carried out by heating for 24 hours.
尚、上記反応は、テトラヒドロフラン（ＴＩＩＦ＞、ジ
エチルエーテル、ジオキサンなどの不活性溶媒の下で行
なうことができ、又、モレキコラーシーブを共存させる
ことが望ましい。The above reaction can be carried out in the presence of an inert solvent such as tetrahydrofuran (TIIF), diethyl ether, dioxane, etc., and it is preferable to coexist with a molecular sieve.
本発明によれば、カルバミン酸エステルから容易に、か
つ高収率でオキサシロン化合物を製造することができる
。又副生物もほとんどないので単離精製も容易である。According to the present invention, oxacilone compounds can be easily produced from carbamate esters in high yield. Furthermore, since there are almost no by-products, isolation and purification is easy.
次に実施例により本発明を具体的に説明する。Next, the present invention will be specifically explained with reference to Examples.
実施例１
１．３−ジブロモ−２−プロピルフェニルカーバメート
のＴ ＨＦ溶液に４Δモレキユラーシーブス存在下２．
５当量のｎ −Ｂｕ４ＮＦ ・３）１２０ （ＴＢＡＦ
）を作用させ５０℃で２４時間攪拌して環化させた。Example 1 1. A THF solution of 3-dibromo-2-propylphenyl carbamate in the presence of 4Δ molecular sieves.
5 equivalents of n-Bu4NF ・3) 120 (TBAF
) and stirred at 50°C for 24 hours to cyclize.
後処理後ＰＬＣにより単離したところ、目的物である下
記の５−メチル−３−フェニル−２（３Ｈ）−オキサシ
ロンが７９％の収率で得られた。又、出発原料として３
−ジクロロ−２−プロピルフェニルカルバメートを用い
、かつ４．０当ＭのＴＢＡＦを用いた以外は同様にして
室温下で処理したところ目的化合物の中間体が７６％の
収率で得られた。After post-treatment, the product was isolated by PLC, and the desired product, 5-methyl-3-phenyl-2(3H)-oxacilone shown below, was obtained in a yield of 79%. Also, as a starting material, 3
-Dichloro-2-propylphenyl carbamate and 4.0 equivalent M of TBAF were used, but the same procedure was carried out at room temperature to obtain an intermediate of the desired compound in a yield of 76%.
これをさらにＴＢＡＦと５０℃で処理することにより容
易に異性化し、目的化合物である５−メチル−３−フェ
ニル−２（３Ｈ）−オキサシロンが７２％の収率で得ら
れた。This was further treated with TBAF at 50°C to easily isomerize, and the target compound, 5-methyl-3-phenyl-2(3H)-oxacilone, was obtained in a yield of 72%.
生成物の同定データを次に示す。Product identification data is shown below.
目的化合物：
ＮＭＲ（［’ＤＣ１，） ： δ ２．１８
（ｄ、 ３Ｈ％ Ｊ＝１．８５１１ｚ） 、６．５７
（ｑ、 Ｉ ＨＳＪ＝１，８０１１ｚ ） 、７．
２０−７．６２ （ｍ１５ Ｈ）
Ｉ Ｒ（ＫＯｒ） ： １７５０ （ｓｈ）
、 １７４０、１６８５．１５９５．１５００．１４０
０．１３８０．１１２０．９７０．７５５．６８０実施
例２
出発原料をかえ、実施例１と同様にしてオキサシロン化
合物を製造した。使用原料、使用したＴ ＢへＦの当量
、生成物及び収率をまとめて表−１に示す。Target compound: NMR (['DC1,): δ 2.18
(d, 3H% J=1.8511z), 6.57
(q, IHSJ=1,8011z), 7.
20-7.62 (m15 H) IR (KOr): 1750 (sh)
, 1740, 1685.1595.1500.140
0.1380.1120.970.755.680 Example 2 An oxacylone compound was produced in the same manner as in Example 1 except that the starting materials were changed. The raw materials used, the equivalent amount of F to TB used, the products, and the yields are summarized in Table 1.
次に生成物の同定データを次に示す。Next, the identification data of the product is shown below.
Ｎｏ、 １、Ｎｏ、 ２の生成化合物：ＮＭＩＩＩ
（ＣｌＩＣＡ、） ：δ２．１６ （ｄ、 ３Ｈ，
Ｊ＝１．８０ｆｉｚ） 、６．５３ （ｑ 、 ｌ
Ｈ，Ｊ ＝１．８０１１ｚ） ７．２０−７．５６（ｍ
、４Ｈ）
ＩＲ（に口ｒ） ： １７６０（ｓｈ） 、１７
４０．１６８０．１５９０ 。No. 1, No. 2 product compounds: NMIII
(ClICA,): δ2.16 (d, 3H,
J=1.80fiz), 6.53 (q, l
H, J = 1.8011z) 7.20-7.56 (m
, 4H) IR (Niguchi r): 1760 (sh), 17
40.1680.1590.
１４９５．１３９０．１２８０．１２００．１１２０．
９７０．７２５Ｎｏ、 ３ の生成化合物：
ＮＭＲ（Ｃ口ＣＬ）： δ ２．２２ （ｄ、
３ １−１ 、 Ｊ＝１，８０Ｉｌｚ） 、６．４２
（ｑ、 Ｌ Ｈ，Ｊ ＝１，８０１１ｚ）、７．４
０−８．００（ｍ、７Ｈ）1495.1390.1280.1200.1120.
970.725No, 3 product compound: NMR (C port CL): δ 2.22 (d,
3 1-1, J=1,80Ilz), 6.42
(q, L H, J = 1,8011z), 7.4
0-8.00 (m, 7H)
Claims (2)
I ） （式中、Ｒ＿１は炭化水素基を示し、Ｘはハロゲンを示
す。） で表わされるカルバミン酸エステルを、フッ素イオンの
存在下でオレフィン生成をともない環化させることを特
徴とする一般式（II）： ▲数式、化学式、表等があります▼……………………（
II） （式中Ｒ＿１及びＸは式（ I ）と同じ意味を有する。
） で表わされるオキサゾロン化合物の製造方法。(1) General formula (I): ▲There are mathematical formulas, chemical formulas, tables, etc.▼…………………………(
I) (In the formula, R_1 represents a hydrocarbon group and X represents a halogen.) The general formula ( II): ▲There are mathematical formulas, chemical formulas, tables, etc.▼……………………(
II) (In the formula, R_1 and X have the same meaning as in formula (I).
) A method for producing an oxazolone compound represented by
基、アルケニル基又は芳香族基を示す。）で表わされる
第４級アンモニウム塩に由来する特許請求の範囲第（１
）項記載の製造方法。(2) Fluorine ion has the general formula (III): ▲There are mathematical formulas, chemical formulas, tables, etc.▼…………………… (III) (In the formula, R_2 to R_5 are alkyl groups or alkenyl groups having 1 to 16 carbon atoms. or aromatic group) is derived from the quaternary ammonium salt represented by
) The manufacturing method described in section 2.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4704786A JPS62205065A (en) | 1986-03-04 | 1986-03-04 | Production of oxazolone compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4704786A JPS62205065A (en) | 1986-03-04 | 1986-03-04 | Production of oxazolone compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62205065A true JPS62205065A (en) | 1987-09-09 |
Family
ID=12764253
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4704786A Pending JPS62205065A (en) | 1986-03-04 | 1986-03-04 | Production of oxazolone compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62205065A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016088893A (en) * | 2014-11-05 | 2016-05-23 | 国立研究開発法人産業技術総合研究所 | 2-oxazolones and manufacturing method of 2-oxazolones |
-
1986
- 1986-03-04 JP JP4704786A patent/JPS62205065A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2016088893A (en) * | 2014-11-05 | 2016-05-23 | 国立研究開発法人産業技術総合研究所 | 2-oxazolones and manufacturing method of 2-oxazolones |
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