JPS63222156A - Beta-lactam intermediate - Google Patents
Beta-lactam intermediateInfo
- Publication number
- JPS63222156A JPS63222156A JP62055963A JP5596387A JPS63222156A JP S63222156 A JPS63222156 A JP S63222156A JP 62055963 A JP62055963 A JP 62055963A JP 5596387 A JP5596387 A JP 5596387A JP S63222156 A JPS63222156 A JP S63222156A
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- compound according
- formula
- trialkylsilyl
- 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
- 150000003952 β-lactams Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 3
- 125000001931 aliphatic group Chemical group 0.000 claims abstract 2
- -1 t-butyldimethylsilyl group Chemical group 0.000 claims description 22
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 abstract description 7
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract description 2
- 239000003782 beta lactam antibiotic agent Substances 0.000 abstract description 2
- 239000011734 sodium Substances 0.000 abstract description 2
- 229910052708 sodium Inorganic materials 0.000 abstract description 2
- 239000002132 β-lactam antibiotic Substances 0.000 abstract description 2
- 229940124586 β-lactam antibiotics Drugs 0.000 abstract description 2
- GWHDKFODLYVMQG-UHFFFAOYSA-N [3-[1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl] acetate Chemical compound CC(C)(C)[Si](C)(C)OC(C)C1C(OC(C)=O)NC1=O GWHDKFODLYVMQG-UHFFFAOYSA-N 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- JQZIKLPHXXBMCA-UHFFFAOYSA-N triphenylmethanethiol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(S)C1=CC=CC=C1 JQZIKLPHXXBMCA-UHFFFAOYSA-N 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
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、３位に水酸基が保護されたとドロキシエチル
基を有し、４位にアルコキシ基を有する一般式（１）
く式中、Ｒ１は水酸基の保護基、Ｒ２は水素またはアミ
ノ基の保護基、Ｒ３は０１〜Ｃ４の脂肪族炭化水素を表
す）
で示される新規なβ−ラクタム化合物に関する。Detailed Description of the Invention (Industrial Application Field) The present invention relates to a compound of general formula (1) having a protected hydroxyl group and a hydroxyethyl group at the 3-position and an alkoxy group at the 4-position. The present invention relates to a novel β-lactam compound represented by a hydroxyl group-protecting group, R2 is hydrogen or an amino group-protecting group, and R3 is an aliphatic hydrocarbon of 01 to C4.
本発明による新規なβ−ラクタム化合物は４位に反応性
に富むアルコキシ基を有し、種々の誘導体に変換できる
有用な中間体である。例えば、本発明化合物の４位のア
ルコキシ基に置換反応を行なうことにより、ペネム系抗
生物質製造に有用な３−トリフェニルメチルチオアゼチ
ジン−２−オンが取得できる。The novel β-lactam compound according to the present invention has a highly reactive alkoxy group at the 4-position and is a useful intermediate that can be converted into various derivatives. For example, by performing a substitution reaction on the alkoxy group at the 4-position of the compound of the present invention, 3-triphenylmethylthioazetidin-2-one, which is useful for producing penem antibiotics, can be obtained.
（発明が解決しようとする問題点）
従来、４位にアルコキシ基を有する一般式（１）で示さ
れるβ−ラクタム化合物は知られていない。(Problems to be Solved by the Invention) Conventionally, a β-lactam compound represented by the general formula (1) having an alkoxy group at the 4-position has not been known.
本発明者らは、このβ−ラクタムがペネム系β−ラクタ
ム抗生物質の有用な合成中間体になりうろことに着目し
、その合成法を確立して本発明を完成した。The present inventors focused on the fact that this β-lactam could be a useful synthetic intermediate for penem β-lactam antibiotics, established a method for its synthesis, and completed the present invention.
（問題点を解決するための手段及び作用効果）本発明の
前記β−ラクタム化合物を示す一般式（１）中、几１は
水酸基の保護基であり、ｔ−ブチルジメチルシリル基、
トリイソプロピルシリル基、アセチル基、ベンジルオキ
シカルボニル基、ｏ−ニトロベンジルオキシカルボニル
基、ｐ−ニトロベンジルオキシカルボニル基、ｔ−ブチ
ル基等が挙げられ、Ｒ２は水素、またはアミノ基の保護
基であり、ｔ−ブチルジメチルシリル基、トリイソプロ
ピルシリル基、トリメチルシリル基、アセチル基、ベン
ジルオキシカルボニル基、０−ニトロベンジルオキシカ
ルボニル基、ｐ−ニトロベンジルオキシカルボニル基等
が挙げられる。これらの中で殊に好適なのはｔ−ブチル
ジメチルシリル基、トリイソプロピルシリル基に代表さ
れるトリアルキルシリル基である。これらのトリアルキ
ルシリル基は一般式（１）で示されるβ−ラクタム化化
合合物合成時、安定であり、目的のβ−ラクタム化合物
を取得後、比較的容易に脱保護できる。また、几３はメ
チル基、エチル基等に代表されるｃｌ −ｃ４の脂肪族
炭化水素であり、好ましくはメチル基が用いられる。(Means and effects for solving the problems) In the general formula (1) showing the β-lactam compound of the present invention, 几1 is a hydroxyl group protecting group, t-butyldimethylsilyl group,
Examples include triisopropylsilyl group, acetyl group, benzyloxycarbonyl group, o-nitrobenzyloxycarbonyl group, p-nitrobenzyloxycarbonyl group, t-butyl group, and R2 is hydrogen or a protecting group for amino group. , t-butyldimethylsilyl group, triisopropylsilyl group, trimethylsilyl group, acetyl group, benzyloxycarbonyl group, 0-nitrobenzyloxycarbonyl group, p-nitrobenzyloxycarbonyl group, and the like. Among these, particularly preferred are trialkylsilyl groups such as t-butyldimethylsilyl group and triisopropylsilyl group. These trialkylsilyl groups are stable during the synthesis of the β-lactam compound represented by the general formula (1), and can be relatively easily deprotected after obtaining the desired β-lactam compound. Moreover, 几3 is a cl-c4 aliphatic hydrocarbon represented by a methyl group, an ethyl group, etc., and preferably a methyl group is used.
本発明化合物である新規な４位にアルコキシ基を有する
β−ラクタム化合物の有用性は、参考例に示すように、
既に例えばヘテロシクリルペネムの有用中間体として知
られている（特開昭６１−２４８０８８ ）、８（Ｉｔ
）−（１−ヒドロキシエチル）−４（Ｒ）−トリフェニ
ルメチルチオアゼチジン−２−オン化合物に変換できる
。The usefulness of the novel β-lactam compound having an alkoxy group at the 4-position, which is a compound of the present invention, is demonstrated by the following reference examples:
For example, it is already known as a useful intermediate for heterocyclylpenem (Japanese Patent Application Laid-Open No. 61-248088), 8 (It
)-(1-hydroxyethyl)-4(R)-triphenylmethylthioazetidin-2-one compound.
次に本発明化合物の製造法を説明する。Next, a method for producing the compound of the present invention will be explained.
従来まで、３位に水酸基が保護されたヒドロキシエチル
基を有し、４位にアルコキシ基を有するβ−ラクタム化
合物の合成については知られていなかった。本発明者ら
は下記に示す反応式により４位アルコキシ−β−ラクタ
ム化合物が生成することを見出した。Until now, it has not been known to synthesize a β-lactam compound having a hydroxyethyl group with a protected hydroxyl group at the 3-position and an alkoxy group at the 4-position. The present inventors have discovered that a 4-position alkoxy-β-lactam compound is produced according to the reaction formula shown below.
（式中、１１ 、 Ｒ２，几３は前記に同じ）即ち、特
開昭６１−１８７９１の方法により得ることのできる８
−ｊ：Ｉ−（ｔ−ブチルジメチルシロキシ）エチルクー
４−アセトキシアビチジン−２−オンを原料として用い
、アルカノール中、は室温で十分であり、８−ＣＩ−（
ｔ−ブチルジメチルシロ）キシエチル〕−４−アセトキ
シアゼチジン−２−オンとナトリウムアルコラードのモ
ル比はＩ：ｌの当モル比が採用される。反応時間は通常
数時間から一日の範囲で実施される。精製は、溶媒留去
後、ヘキサンによる抽出・結晶化により単離できる。(In the formula, 11, R2, and 3 are the same as above) That is, 8 which can be obtained by the method of JP-A-61-18791.
-j: I-(t-butyldimethylsiloxy)ethylcou-4-acetoxyavitidin-2-one is used as a raw material, in alkanol, room temperature is sufficient, and 8-CI-(
The molar ratio of t-butyldimethylsilyl)oxyethyl]-4-acetoxyazetidin-2-one and sodium alcoholade is an equimolar ratio of I:l. The reaction time is usually in the range of several hours to one day. For purification, isolation can be achieved by distilling off the solvent, followed by extraction with hexane and crystallization.
（実施例）
以下、実施例により本発明を更に具体的に説明するが、
本発明はこれらの実施例のみで限定されるものではない
。(Example) Hereinafter, the present invention will be explained in more detail with reference to Examples.
The present invention is not limited only to these examples.
実施例１
（３Ｒ，４几、５Ｒ）−３−ＣＩ−（ｔ−ブチルジメチ
ルシロキシ）エチルシー４−メトキシ−アゼチジン−２
−オンの合成
ナトリウム２５ｍ、９をメタノール２ｍｊ７に室温で加
え、１時間撹拌した。次に（８Ｉ’Ｌ、４ＥＬ。Example 1 (3R,4L,5R)-3-CI-(t-butyldimethylsiloxy)ethylcy4-methoxy-azetidine-2
-25m, 9 of synthetic sodium chloride was added to 2mj7 of methanol at room temperature and stirred for 1 hour. Next (8I'L, 4EL.
５Ｒ）−３−［： ｌ−（ｔ−ブチルジメチルシリロキ
シ）エチル〕−４−アセトキシアゼチジン−２−オン２
８７ｍ、ｐを０〜１０℃で添加し、室温で１０時間撹拌
した。反応混合物をエーテル２０ｍｌ、飽和塩化アンモ
ニウム水溶液１０ｍＪの混合溶液へ移し、１０分撹拌し
た。エーテル溶液を飽和食塩水で洗浄し、硫酸マグネシ
ウムで乾燥後、エーテルを減圧留去すると粗生成物とし
て白色粉末が得られた。得られた粗生成物はヘキサンよ
り再結晶して２２ （ｉ ｍ、ｉ；１１の目的とする４
−メトキシ体を得た（収率８７％）。このものの理化学
的性状は以下の通りである。5R)-3-[: l-(t-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 2
87m,p was added at 0-10°C and stirred at room temperature for 10 hours. The reaction mixture was transferred to a mixed solution of 20 ml of ether and 10 mJ of a saturated aqueous ammonium chloride solution, and stirred for 10 minutes. The ether solution was washed with saturated brine, dried over magnesium sulfate, and the ether was distilled off under reduced pressure to obtain a white powder as a crude product. The obtained crude product was recrystallized from hexane to obtain the desired 4
-methoxy compound was obtained (yield 87%). The physical and chemical properties of this product are as follows.
〔ａ〕＝ −６，９°（ｃ ＝ ０．８４ 、 Ｍｅｎ
ｕ）Ｉ Ｈ−ＮＭＲ（９０ＭＨｚ 、ＣＤＣ１ｇ ）
δ（ｐｐｍ）０．０８（６Ｈ，ｓ）、０．９０（９Ｈ
。[a] = -6,9° (c = 0.84, Men
u) IH-NMR (90MHz, CDC1g)
δ (ppm) 0.08 (6H, s), 0.90 (9H
.
Ｓ）、１．２７（８Ｈ，ｄ）、３．０５（ＩＨ，ｄｄ）
、８．３７（３Ｈ，Ｓ）、４．１３ （Ｉ Ｈ、ｍ）、
４．９５（Ｉｎ。S), 1.27 (8H, d), 3.05 (IH, dd)
, 8.37 (3H, S), 4.13 (I H, m),
4.95 (In.
ｄ）、６．６４ （Ｉ Ｈ、ｂｒｏａｄ）ｍｐ５７−５
７．５℃
参考例
（８Ｒ，４Ｉｔ、５Ｒ） −３−［：１−（ｔ−ブチル
ジメチルシロキシ）エチル〕−４−トリフェニルメチル
チオアゼチジン−２−オンの合成（３Ｒ，４Ｒ，５几）
−１−ＣＩ−（ｔ−ブチルジメチルシロキシ）エチルシ
ー４−メトキシ−アゼチジン−２−オンの塩化メチレン
溶液（１０ｍｌ 、 ２０．５ ｍｍｏｌ ） ヘ−
７０℃で四塩化チタン２２５μ１（２０，５皿ｏ１）を
加え、続いてトリエチルアミン３４３ ａｌ（２４，６
ｍｍｏｌ）、及びトリフェニルメタンチオール８４８
ｍｌ （８０，７ｍｍｏｌ ）。d), 6.64 (IH, broad) mp57-5
7.5°C Reference Example (8R, 4It, 5R) Synthesis of -3-[:1-(t-butyldimethylsiloxy)ethyl]-4-triphenylmethylthioazetidin-2-one (3R, 4R, 5R) )
-1-CI-(t-butyldimethylsiloxy)ethyl-4-methoxy-azetidin-2-one in methylene chloride solution (10 ml, 20.5 mmol)
Add 225 μl of titanium tetrachloride (20,5 plates o1) at 70°C, followed by 343 al of triethylamine (24,6 plate o1).
mmol), and triphenylmethanethiol 848
ml (80,7 mmol).
を添加した。ゆっくりと室温まで昇温させ、室温で１０
時間撹拌した。反応混合物を酢酸エチル３９ｍ１．
飽和塩化アンモニウム水溶液２０ｍＪの混合溶液中へ移
し、１０分撹拌した。酢酸エチル相を硫酸マグネシウム
で乾燥後、酢酸エチルを減圧留去し、シリカゲルカラム
（ヘキサンニア七トン＝２０ ： １ ）で溶出すると
目的の４−トリフェニルメチルチオアゼチジン誘導体６
２８ｍ、９を得た（収率６１％）。was added. Slowly raise the temperature to room temperature, and keep at room temperature for 10 minutes.
Stir for hours. The reaction mixture was diluted with 39 ml of ethyl acetate.
It was transferred into a mixed solution of 20 mJ of saturated ammonium chloride aqueous solution and stirred for 10 minutes. After drying the ethyl acetate phase with magnesium sulfate, ethyl acetate was distilled off under reduced pressure and eluted with a silica gel column (7 tons of hexane = 20:1) to obtain the desired 4-triphenylmethylthioazetidine derivative 6.
28m, 9 was obtained (yield 61%).
〔α］＝＋３．７° （ｃ＝８．０ 、 ＣＨＯｌａ）
Ｉ Ｈ−ＮＭＲ（９０ＭＨｚ 、ＣＤ０１Ｂ） δ（
ｐＩ）ｍ）０．０８（６Ｉ（、Ｓ）、０．８２（９Ｈ，
Ｓ）、１．２７（８Ｈ，ｄ）、８．１０（ＩＥＩ、ｔ）
、４．２０（ＩＨ，ｍ）、４．３６（ＩＨ，ｂｒ。[α]=+3.7° (c=8.0, CHOla)
IH-NMR (90MHz, CD01B) δ(
pI)m) 0.08 (6I(,S), 0.82(9H,
S), 1.27 (8H, d), 8.10 (IEI, t)
, 4.20 (IH, m), 4.36 (IH, br.
Ｓ）、４．５５（ＩＨ，ｄ）、７．４２（１５Ｈ。S), 4.55 (IH, d), 7.42 (15H.
ｍ） ｍｐ９Ｂ−９６℃m) mp9B-96℃
Claims (6)
アミノ基の保護基、Ｒ＾３はＣ＿１〜Ｃ＿４の脂肪族炭
化水素を表す） で示される光学活性４−アルコキシアゼチジン−２−オ
ン化合物。(1) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R^1 is a hydroxyl group protecting group, R^2 is a hydrogen or amino group protecting group, R^3 is an aliphatic group of C_1 to C_4 An optically active 4-alkoxyazetidin-2-one compound represented by (representing a hydrocarbon).
テトラヒドロピラニル基、ベンジル基またはｐ−ニトロ
ベンジル基である特許請求の範囲第１項記載の化合物。(2) R^1 is a trialkylsilyl group, t-butyl group,
The compound according to claim 1, which is a tetrahydropyranyl group, a benzyl group or a p-nitrobenzyl group.
ドロピラニル基、ベンジル基、ｐ−ニトロベンジル基で
ある特許請求の範囲第１項記載の化合物。(3) The compound according to claim 1, wherein R^2 is hydrogen, trialkylsilyl group, tetrahydropyranyl group, benzyl group, or p-nitrobenzyl group.
載の化合物。(4) The compound according to claim 1, wherein R^3 is a methyl group.
ル基、トリイソプロピルシリル基、トリメチルシリル基
、ｔ−ブチルフェニルメチル基である特許請求の範囲第
２項記載の化合物。(5) The compound according to claim 2, wherein the trialkylsilyl group is a t-butyldimethylsilyl group, a triisopropylsilyl group, a trimethylsilyl group, or a t-butylphenylmethyl group.
ル基、トリイソプロピルシリル基、トリメチルシリル基
、ｔ−ブチルフェニルメチル基である特許請求の範囲第
３項記載の化合物。(6) The compound according to claim 3, wherein the trialkylsilyl group is a t-butyldimethylsilyl group, a triisopropylsilyl group, a trimethylsilyl group, or a t-butylphenylmethyl group.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62055963A JPS63222156A (en) | 1987-03-11 | 1987-03-11 | Beta-lactam intermediate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP62055963A JPS63222156A (en) | 1987-03-11 | 1987-03-11 | Beta-lactam intermediate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63222156A true JPS63222156A (en) | 1988-09-16 |
Family
ID=13013737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62055963A Pending JPS63222156A (en) | 1987-03-11 | 1987-03-11 | Beta-lactam intermediate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63222156A (en) |
-
1987
- 1987-03-11 JP JP62055963A patent/JPS63222156A/en active Pending
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