JPS58126894A - Preparation of 2-azetidinone derivative - Google Patents
Preparation of 2-azetidinone derivativeInfo
- Publication number
- JPS58126894A JPS58126894A JP57009812A JP981282A JPS58126894A JP S58126894 A JPS58126894 A JP S58126894A JP 57009812 A JP57009812 A JP 57009812A JP 981282 A JP981282 A JP 981282A JP S58126894 A JPS58126894 A JP S58126894A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- azetidinone derivative
- aldehyde
- allyl
- 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
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 4
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 12
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 abstract description 8
- -1 carbapenem compound Chemical class 0.000 abstract description 7
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 6
- 229910000489 osmium tetroxide Inorganic materials 0.000 abstract description 5
- 239000012285 osmium tetroxide Substances 0.000 abstract description 5
- 239000007858 starting material Substances 0.000 abstract description 4
- RNKLLZTVWHLOJG-UHFFFAOYSA-N 4-prop-2-enylazetidin-2-one Chemical class C=CCC1CC(=O)N1 RNKLLZTVWHLOJG-UHFFFAOYSA-N 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 3
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 239000003814 drug Substances 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
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 229940041011 carbapenems Drugs 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Chemical class 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical group CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 238000006052 Horner reaction Methods 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001576 beta-amino acids Chemical class 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- YZBQHRLRFGPBSL-RXMQYKEDSA-N carbapenem Chemical class C1C=CN2C(=O)C[C@H]21 YZBQHRLRFGPBSL-RXMQYKEDSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical class [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】 本発明は、２−アゼチジノン誘導体の製法に関する。[Detailed description of the invention] The present invention relates to a method for producing 2-azetidinone derivatives.
近年、有用な生物活性を有するチェナマイシンが見出さ
れたのを契機として、抗菌剤として有用なカルバペネム
化合物を合成しようとする試みが盛んになされている。In recent years, with the discovery of chenamycin having useful biological activity, many attempts have been made to synthesize carbapenem compounds useful as antibacterial agents.
カルバペネム類はその構造式から明らかなように種々の
光学異性体が存在するが、抗菌剤として有用なものはあ
る特定の立体構造を有する光学活性体であることがわか
っている。As is clear from their structural formulas, carbapenems exist in various optical isomers, but it is known that optically active forms with a specific three-dimensional structure are useful as antibacterial agents.
しかしながら、従来得られているカルバペネム類はラセ
ミ体であることがしばしばでちるから、これを更に複雑
な工程からなる分割を経なければ有用な光学活性体を得
ることはできない。However, since conventionally obtained carbapenems are often racemic, useful optically active forms cannot be obtained unless they are resolved through more complicated steps.
本発明者らは、分割を行なうことなく特定の立体構造を
有する光学活性体を得ようとして柚々研究の結果、必要
とする特定の立体構造を有する４−アリル−２−アゼチ
ジノン誘導体をアルデヒド体となした後ヴイッティッヒ
・ホルナー反応を行なうことによって、その立体構造を
そのまま保持し、医薬として有用なカルバペネム化合物
に容易に変えることができる２−アゼチジノン誘導体を
得ることに成功し、本発明を完成した。As a result of extensive research in an attempt to obtain an optically active compound having a specific steric structure without performing resolution, the present inventors discovered that a 4-allyl-2-azetidinone derivative having the required specific steric structure was converted into an aldehyde derivative. By carrying out the Wittich-Horner reaction after forming the 2-azetidinone derivative, they succeeded in obtaining a 2-azetidinone derivative that retains its steric structure and can be easily converted into a carbapenem compound useful as a pharmaceutical, thereby completing the present invention. .
本発明は、
式
％式％
）
で表わされる化合物（以下、化合物Ｉと称する。）を、
その４位のアリル基を酸化することによって対応するア
ルデヒド体（以下、化合物■と称する。）とした後、こ
れをウィノティ、ヒ・ホル丈−試楽と反応させて、
ＯＨ３Ｓｉ ＣＨ３
Ｃ（ＣＨ３）３
で表わされる化合物（以下、化合物■と称する。）とす
ることを特徴とする２−アゼチジノンｂ導体の製法であ
る。The present invention provides a compound represented by the formula (% formula %) (hereinafter referred to as compound I),
The allyl group at the 4-position is oxidized to form the corresponding aldehyde (hereinafter referred to as compound ■), and this is then reacted with Winoti and Hi-Horjo-Jiraku to form OH3Si CH3 C(CH3)3 This is a method for producing a 2-azetidinone b conductor, which is characterized by using a compound represented by (hereinafter referred to as compound (2)).
本発明において、出発原料である化合物夏０４位のアリ
ル基の酸化は、たとえば、含水テトラヒドロフラン中で
四酸化オスミウムと過ヨウ素酸ナトリウムの系で酸化す
ることにより行なう。In the present invention, the oxidation of the allyl group at the 04-position of the starting material compound is carried out, for example, by oxidation in a system of osmium tetroxide and sodium periodate in aqueous tetrahydrofuran.
その結果、
０（ＯＨ３）３１
で表わされるアルデヒド体（化合物■）が得られる。っ
また、ヴイ、ティッヒ・ホルナー試薬は、アルゴン気流
中、水冷下に水素化ア／ｌカリ金属化合物（たとえば、
水素化ナトリウム、水素化カリウムなど）、リチウム金
属化合物（たとえば、ブチルリチウム、フェニルリチウ
ムなと）などの強塩基をジアルキル ペンジルオキンア
セチルフォスフォネート（たとえば、ジメチル ベンジ
ルオキンアセチルフォスフォネート、／エテル ベンジ
ルオキンアセチルフォスフォネ−１７ｉ１．ど）とを反
応させることによって得られる化合物を意味する。As a result, an aldehyde (compound ■) represented by 0(OH3)31 is obtained. Furthermore, the Tych-Horner reagent is a mixture of hydrogenated alkali metal compounds (e.g.,
(e.g., sodium hydride, potassium hydride, etc.), lithium metal compounds (e.g., butyllithium, phenyllithium, etc.). /Ether means a compound obtained by reacting benzyl oxine acetylphosphone-17i1., etc.).
本発明の目的化合物である化合物■は、たとえば次の方
法により製造することができる。Compound (1), which is the target compound of the present invention, can be produced, for example, by the following method.
すなわち、出発原料である化合物１を含水テトラヒドロ
フラン中で、冷却子四酸化オスミウムと過ヨウ素酸ナト
リウムで酸化し、生成したアルデヒド体（化合物■）を
単離することなく、その反尾、液を別に予め前記方法で
調製したヴイッティンヒ・ホルナー試薬の溶液中に強冷
上滴下して反応させ、目的とする化合物■を製造するこ
とができる。That is, Compound 1, which is a starting material, is oxidized with a cooler of osmium tetroxide and sodium periodate in aqueous tetrahydrofuran, and the resulting aldehyde (compound ■) is oxidized without isolating it and the liquid is separated. The target compound (1) can be produced by dropping it dropwise into a solution of the Wittting-Horner reagent prepared in advance by the above method on strong cooling and causing a reaction.
出発物質である化合物Ｉは、次の方法により製造するこ
とができる。Compound I, which is a starting material, can be produced by the following method.
すなわち、
で表わされる化合物を、そのアミン基の保護基を脱離し
て対応するβ−アミノ酸とした後、これを閉環すること
により、
で表わされる化合物（以下、化合物■と称する。）とな
し、この化合物■とターシャリイプチルジメチルンリル
クロリドとを常法により反応させることにより化合物Ｉ
を製造することができる。That is, a compound represented by the following is converted into a corresponding β-amino acid by removing the protecting group of its amine group, and then ring-closed to form a compound represented by the following (hereinafter referred to as compound ①), By reacting this compound (1) with tert-iptyldimethyltrichloride in a conventional manner, compound I is obtained.
can be manufactured.
本発明の方法により、抗菌性を有する、光学活性構造の
アザビシ’Ａ〔５，２，０）ヘプテン環を有するカルバ
ペネム化合物（たとえは、アザビシクロ（３，２，Ｏ〕
〕ヘプトー２−エンー２−カルボン酸を合成する原料と
して有用な化合物■を、光学分割などの？ｉｔｈな工程
を経ることなく原料化合物の立体構造を保持したまま効
率よく製造することができる。By the method of the present invention, a carbapenem compound having an optically active structure azabicyclo(3,2,0) heptene ring (for example, azabicyclo(3,2,O)
] Compound ■ useful as a raw material for synthesizing hept-2-ene-2-carboxylic acid, by optical resolution, etc.? It can be efficiently produced while maintaining the three-dimensional structure of the raw material compound without going through any additional steps.
以下、化合物■からの化合物１の製造例を示す参考例、
および化合物Ｉからの化合物■の製造例を不す実施例を
挙けて本発明を具体的に説明する。Below, a reference example showing an example of the production of compound 1 from compound ■,
The present invention will be specifically explained with reference to Examples excluding the preparation of Compound (1) from Compound (1) and Compound (I).
参考例
化合物■６６６■（６ｒｒｍｏｔ ）およびターンヤリ
イブチルジメチルンリルクロリド９０５〜（６ｍｒｎｏ
ｔ）のジメチルホルムアミド２０ｍ１溶液に、アルゴン
気流下、０℃でトリエチルアミン１ ｍｌ（７，２ｍｍ
ｏｔ）を加え、同温下で３０分間攪拌後、この反応液に
水８０ｄ’ｉ加え、ジエチルエーテルで抽出した。Reference example compound ■666■ (6rrmot) and turnybutyldimethyltrichloride 905~(6mrno
Add 1 ml of triethylamine (7.2 mm
After stirring at the same temperature for 30 minutes, 80 d'i of water was added to the reaction solution, and the mixture was extracted with diethyl ether.
この有機層を飽和食塩水で洗浄し、芒硝で乾燥後、減圧
下、溶媒を留去し、油状物１４１２を侍、これをシリカ
ゲル１４９を用いてカラムクロマトグラフィーに付し、
ジエチルエーテル−ヘキサン（５： Ｉ Ｖ／Ｖ）混合
液の流分より、無色油状物として化合物１１．２２９を
得た。This organic layer was washed with saturated brine, dried over sodium sulfate, and the solvent was distilled off under reduced pressure to obtain an oily substance 1412, which was subjected to column chromatography using silica gel 149.
Compound 11.229 was obtained as a colorless oil from the diethyl ether-hexane (5:IV/V) mixture.
収率 ９０％
Ｎ Ｍ Ｒ（ｃＤｃｚ３）
δｐｐｍ ： ４．８３〜６．１０ （３Ｈ，ｍ ）、
３．３７〜３．８５（Ｉ Ｈ，ｍ ）、 １．８３〜３
．２３ （４Ｈ，ｍ）。Yield 90% NMR (cDcz3) δppm: 4.83-6.10 (3H,m),
3.37-3.85 (IH,m), 1.83-3
．． 23 (4H, m).
０．８０（９Ｈ，Ｓ）、０．１７（３Ｈ，８）Ｍａｓｓ
（ｍ／ｅ）：１８５（Ｍ”）
実施例
（１）化合物１１．２２２（５，４ｍｍｏｌ ）を３０
％含水テトラヒドロフラン２０−に溶解し、０℃で四酸
化オスミウムのターシャリイブタノール溶液（０，０２
ｍｍｏｔ／ｄ） ２ｍ（０，０４ｍｍ○ｔ）を刃口え、
１司温下で５分間攪拌後、過ヨウ素酸ナトリウムｔ ４
ｔ （６，６ｍｍｏｔ）を３０分かけて加え、更に
１４時間攪拌し、この反応溶液に水５−を加え、ジ
エチルエーテルで抽出した。0.80 (9H, S), 0.17 (3H, 8) Mass
(m/e): 185 (M”) Example (1) Compound 11.222 (5.4 mmol) was added to 30
A solution of osmium tetroxide in tertiary butanol (0,02
mmot/d) 2m (0.04mm○t),
After stirring for 5 minutes at room temperature, sodium periodate t4
t (6,6 mmot) over 30 minutes, and then
After stirring for 14 hours, water was added to the reaction solution, followed by extraction with diethyl ether.
この有機層を飽和食塩水で洗浄し、芒硝で乾燥後、減圧
下で溶媒を留去し、黒色油状物（四酸化オスミウムを含
む）として化合物■（アルデヒド体）を得た。This organic layer was washed with saturated brine, dried over sodium sulfate, and the solvent was distilled off under reduced pressure to obtain Compound (1) (aldehyde) as a black oil (containing osmium tetroxide).
これを単離、精製することなく次の反応に使用する。This is used in the next reaction without isolation or purification.
（２）５０％水素化ナトリウム２５７ ＋ｙ（５，３７
ｍｍｏｔ）をヘキサンで洗浄し、これにテトラヒドロフ
ラン５−を加え、ついでアルゴン気流中、メタノール−
水冷下、ジエチル ベンジルオキシアセチルフォスフォ
ネート１，５４ｒ（５，３７ｍｍｏｔ）のテトラヒドロ
フラン溶液２−を滴下し、同温下で３０分間攪拌後、こ
の反応溶液を一７８℃に冷却し、これに前項（１）で得
た化合物１１１．２２１ｉ’（５，５７ｍｍｏｔ）のテ
トラヒドロフラン浴’Ｑ５１ｎｌを滴下し、同温度で３
０分間、更ＫＯ℃で６０分間指押し、反応溶液に飽和塩
化アンモニア水溶ｉ２ｍＡ’を加えて数分間攪拌後、水
層を分離し、有機層を飽和食塩水で洗浄し、芒硝で乾燥
した。(2) 50% sodium hydride 257 +y(5,37
mmot) was washed with hexane, tetrahydrofuran 5- was added thereto, and then methanol-
Under cooling with water, a tetrahydrofuran solution 2- of diethyl benzyloxyacetylphosphonate 1,54r (5,37 mmot) was added dropwise, and after stirring at the same temperature for 30 minutes, the reaction solution was cooled to -78°C, and added to the above solution. Compound 111.221i' (5,57 mmot) obtained in (1) was added dropwise to 51 nl of tetrahydrofuran bath 'Q' at the same temperature.
After 60 minutes of finger pressing at KO°C, saturated ammonium chloride aqueous solution i2mA' was added to the reaction solution, and after stirring for several minutes, the aqueous layer was separated, and the organic layer was washed with saturated brine and dried over Glauber's salt.
これを減圧下、溶媒を留去し、得られた残渣をシリカゲ
ル２０７を用い、カラムクロマトグラフィーに付し、ジ
エチルエーテル流分より黒色油状物として化合物［１１
，４９を得た。The solvent was distilled off under reduced pressure, and the resulting residue was subjected to column chromatography using silica gel 207. Compound [11
,49 was obtained.
収率 ７７１％
工Ｒｖ ｎ０８″ｃｍ−’： １７５５．１７２ＯＮＭ
Ｒ（ｃＤｃｔ３）
δｐｐｍニア、３ （５Ｈ，ｓ ）、 ６．５７〜７．
３ （ＩＨ，ｍ）。Yield 771% Engineering Rv n08″cm-’: 1755.172ONM
R(cDct3) δppm near, 3 (5H,s), 6.57-7.
3 (IH, m).
５．８３ （Ｉ Ｈ，ｂｒ、ｄ、 Ｊ＝１４ Ｈｚ）
。5.83 (IH, br, d, J=14 Hz)
.
５．１０ （２Ｈ，ｓ ）、 ３．３７〜３．８０（Ｉ
Ｈ。5.10 (2H,s), 3.37-3.80 (I
H.
ｍ ）、 １．９０〜ｉ３７ （４Ｈ，ｍ ）、 ０．
７６（９Ｈ，８）、０．１７（３Ｈ，８）
Ｍａｓｓ（ｍ／ｅ）：３６０（Ｍ＋）
Ｃａ ）＋６＝ −２ｓｌｏ （Ｃ＝４．８． ｃａｃ
ｚ３）特許出願人 大正製薬株式会社
代理人 弁理士 北 川 富 造m), 1.90-i37 (4H, m), 0.
76 (9H, 8), 0.17 (3H, 8) Mass (m/e): 360 (M+) Ca ) + 6 = -2slo (C = 4.8. cac
z3) Patent applicant Taisho Pharmaceutical Co., Ltd. Agent Patent attorney Tomizo Kitagawa
Claims (1)
ことによって対応するアノ１、デヒド体とした俊、これ
をグイ、フィ、ヒ・ホルナー試薬と反応させて、 ＯＨ３Ｓｉ ＣＨ３ Ｃ（ＣＨ３遍 で表わされる化合物とすることを特徴とする２−アゼチ
ジノン誘導体の製法。[Scope of Claims] 1) A compound represented by CH3-8i CH3 C(CH3)3 is converted into the corresponding ano-1, dehyde form by oxidizing its 4-position allyl group, , a method for producing a 2-azetidinone derivative, which comprises reacting with Hi-Horner's reagent to produce a compound represented by OH3Si CH3 C (CH3ben).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57009812A JPS58126894A (en) | 1982-01-25 | 1982-01-25 | Preparation of 2-azetidinone derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57009812A JPS58126894A (en) | 1982-01-25 | 1982-01-25 | Preparation of 2-azetidinone derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS58126894A true JPS58126894A (en) | 1983-07-28 |
Family
ID=11730573
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57009812A Pending JPS58126894A (en) | 1982-01-25 | 1982-01-25 | Preparation of 2-azetidinone derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58126894A (en) |
-
1982
- 1982-01-25 JP JP57009812A patent/JPS58126894A/en active Pending
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