JPH0212233B2 - - Google Patents
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- Publication number
- JPH0212233B2 JPH0212233B2 JP3964481A JP3964481A JPH0212233B2 JP H0212233 B2 JPH0212233 B2 JP H0212233B2 JP 3964481 A JP3964481 A JP 3964481A JP 3964481 A JP3964481 A JP 3964481A JP H0212233 B2 JPH0212233 B2 JP H0212233B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- reaction
- value
- general formula
- fluoride
- 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
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910001506 inorganic fluoride Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- YJRWQNIRFXVBRB-WDYNHAJCSA-N homoaromoline Chemical compound C1C(C=C2)=CC=C2OC(=C2)C(OC)=CC=C2C[C@H](C2=C3)N(C)CCC2=CC(OC)=C3OC2=C(O)C(OC)=CC3=C2[C@H]1N(C)CC3 YJRWQNIRFXVBRB-WDYNHAJCSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 2
- 239000003880 polar aprotic solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- AHLATJUETSFVIM-UHFFFAOYSA-M rubidium fluoride Chemical compound [F-].[Rb+] AHLATJUETSFVIM-UHFFFAOYSA-M 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- YJRWQNIRFXVBRB-UHFFFAOYSA-N Cycleapeltine Natural products C1C(C=C2)=CC=C2OC(=C2)C(OC)=CC=C2CC(C2=C3)N(C)CCC2=CC(OC)=C3OC2=C(O)C(OC)=CC3=C2C1N(C)CC3 YJRWQNIRFXVBRB-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000208421 Ericaceae Species 0.000 description 1
- JYAPBWCAZXNDAR-UHFFFAOYSA-N Oxyacanthine Natural products COc1cc2CCN(C)C3Cc4ccc(Oc5cccc(CC6N(C)CCc7cc(OC)c(OC)c(Oc(c1)c23)c67)c5)c(O)c4 JYAPBWCAZXNDAR-UHFFFAOYSA-N 0.000 description 1
- 241000218201 Ranunculaceae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- HGNHIFJNOKGSKI-WDYNHAJCSA-N oxyacanthine Chemical compound C([C@H]1N(C)CCC=2C=C(C(OC=3C(OC)=C(OC)C=C4CCN(C)[C@H](C=34)CC3=CC=C(C=C3)O3)=CC=21)OC)C1=CC=C(O)C3=C1 HGNHIFJNOKGSKI-WDYNHAJCSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
【発明の詳細な説明】
本発明は有用な薬理作用を有するアルカロイド
であるセフアランチン及びその類似化合物の新規
な製法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel method for producing cephalantin, an alkaloid having useful pharmacological effects, and its analogous compounds.
本発明者らは、一般式
（式中R1及びR2は低級アルキル基を示す）で表
わされる化合物を一般式
Ｘ―（CH2）o−Ｙ （）
（式中Ｘ及びＹはハロゲン原子、ｎは１〜３の整
数を示す）で表わされる化合物と反応させること
により、一般式
（式中R1及びR2は低級アルキル基、ｎは１〜３
の整数を示す）で表わされるセフアランチン及び
その類似化合物を合成することに成功した。 The inventors have determined that the general formula (In the formula, R 1 and R 2 represent a lower alkyl group) A compound represented by the general formula ) by reacting with a compound represented by the general formula (In the formula, R 1 and R 2 are lower alkyl groups, n is 1 to 3
We succeeded in synthesizing cephalantin and its analogous compounds represented by the integer .
出発物質である式のデメチレンセフアランチ
ンは、メギ科、ツヅラフジ科、キンポウゲ科植物
等に分布するオキシアカンチン、ホモアロモリ
ン、セフアラノリンなどから製造することができ
る。 The starting material, demethylene cephalanthine of the formula, can be produced from oxyacanthine, homoaromoline, cephalanoline, etc., which are distributed in plants of the family Berberaceae, ericaceae, Ranunculaceae, etc.
式の化合物の置換基Ｘ及びＹのためのハロゲ
ン原子としては、塩素原子、臭素原子が好まし
く、Ｘ及びＹは同一でも異なつてもよい。 The halogen atom for the substituents X and Y in the compound of the formula is preferably a chlorine atom or a bromine atom, and X and Y may be the same or different.
本発明の反応は無機弗化物の存在下に極性非プ
ロトン溶媒中で行うことが好ましい。無機弗化物
としては弗化セシウム、弗化カリウム、弗化ルビ
ジウム、弗化リチウム、弗化ナトリウムなどが用
いられる。極性非プロトン溶媒としては、ジメチ
ルホルムアミド、ジメチルスルホキシド、ヘキサ
メチルホスホリツクトリアミドなどが用いられ
る。 The reaction of the invention is preferably carried out in a polar aprotic solvent in the presence of an inorganic fluoride. As the inorganic fluoride, cesium fluoride, potassium fluoride, rubidium fluoride, lithium fluoride, sodium fluoride, etc. are used. As the polar aprotic solvent, dimethylformamide, dimethylsulfoxide, hexamethylphosphoric triamide, etc. are used.
本反応を実施するに際しては、系内の空気をア
ルゴンガス、窒素ガス等の不活性ガスで置換して
おくことが好ましい。反応温度は100〜150℃が好
ましい。通常は30分ないし２時間で反応が終了す
る。 When carrying out this reaction, it is preferable to replace the air in the system with an inert gas such as argon gas or nitrogen gas. The reaction temperature is preferably 100 to 150°C. The reaction usually completes in 30 minutes to 2 hours.
実施例 １
淡黄色無晶性粉末のデメチレンセフアランチン
103.3mg（0.174ミリモル）を無水ジメチルホルム
アミド0.75mlに溶解する。この溶液をアルゴンガ
ス気流下に弗化セシウム184.6mg（1.22ミリモル）
に加え、室温で１時間撹拌したのち、無水臭化メ
チレン0.013ml（0.187ミリモル、ｄ＝2.4956）を
加え、110〜120℃で１時間撹拌する。反応終了
後、反応混合物にクロロホルムを加えて希釈し、
弗化セシウムを去する。液を５％水酸化ナト
リウム溶液で洗浄し、無水炭酸カリウムで乾燥し
たのち溶媒を留去すると、残留物105.6mgが得ら
れる。Example 1 Demethylenecephalantin as pale yellow amorphous powder
103.3 mg (0.174 mmol) are dissolved in 0.75 ml of anhydrous dimethylformamide. 184.6 mg (1.22 mmol) of cesium fluoride was added to this solution under a stream of argon gas.
After stirring at room temperature for 1 hour, 0.013 ml (0.187 mmol, d=2.4956) of anhydrous methylene bromide was added, and the mixture was stirred at 110-120°C for 1 hour. After the reaction is complete, chloroform is added to the reaction mixture to dilute it.
Remove cesium fluoride. The liquid was washed with 5% sodium hydroxide solution, dried over anhydrous potassium carbonate, and the solvent was distilled off to obtain 105.6 mg of a residue.
これをシリカゲルカラム・クロマトグラフイ
（５ｇ）を用い、クロロホルム―メタノール
（15：１）混液で溶出して精製すると、茶褐色の
油状物52.8mg（収率50.1％）が得られる。このも
のの薄層クロマトグラフイは、セフアランチン以
外に若干の不純物が存在することを示すが、
NMR値は1C6H6、1CH3COCH3の付加していな
いセフアランチンと一致した。これをベンゼン―
ジエチルエーテル混液に溶解して不溶物を除去し
たのち、ベンゼン―アセトン混液から再結晶する
と、無色プリズム晶のセフアランチン（1C6H6、
1CH3COCH3付加体）25.9mg（収率20.1％）が得
られる。このもののIR値及び薄層クロマトグラ
フイのRf値は標品と一致した。 This was purified using silica gel column chromatography (5 g) and eluted with a chloroform-methanol (15:1) mixture to obtain 52.8 mg (yield 50.1%) of a brown oil. Thin layer chromatography of this product shows that there are some impurities other than cephalantin.
The NMR value was consistent with cephalanthine without addition of 1C 6 H 6 and 1CH 3 COCH 3 . This is benzene-
After dissolving in a diethyl ether mixture to remove insoluble matter, recrystallization from a benzene-acetone mixture yields colorless prismatic crystals of cephalanthine (1C 6 H 6 ,
25.9 mg (yield 20.1%) of 1CH 3 COCH 3 adduct) is obtained. The IR value and Rf value of this product by thin layer chromatography matched those of the standard product.
融点：99〜102℃
比旋光度：〔α〕19 D＋296゜（ｃ＝1.00、CHCl3）
元素分析値：C37H38N2O6・C6H6・
CH3COCH3として
Ｃ Ｈ Ｎ
計算値(%) 74.37 6.78 3.75
実測値(%) 74.23 6.77 3.75
実施例 ２
デメチレンセフアランチン97.7mg（0.164ミリ
モル）を無水ジメチルホルムアミド0.75mlに溶解
する。この溶液をアルゴンガス気流下で弗化セシ
ウム173.5mg（1.14ミリモル）に加え、室温で１
時間撹拌したのち、臭化エチレン0.016ml（0.185
ミリモル）、ｄ＝2.172）を加え、110〜120℃で２
時間撹拌する。反応終了後、反応混合物にクロロ
ホルムを加えて希釈し、弗化セシウムを去す
る。液を５％水酸化ナトリウム溶液で洗浄し、
無水炭酸ナトリウムで乾燥したのち溶媒を留去す
ると、褐色の残留物77.4mgが得られる。 Melting point: 99-102℃ Specific rotation: [α] 19 D +296゜ (c = 1.00, CHCl 3 ) Elemental analysis value: C 37 H 38 N 2 O 6・C 6 H 6・
CH 3 COCH 3 Calculated value (%) 74.37 6.78 3.75 Actual value (%) 74.23 6.77 3.75 Example 2 97.7 mg (0.164 mmol) of demethylene cephalanthine is dissolved in 0.75 ml of anhydrous dimethylformamide. This solution was added to 173.5 mg (1.14 mmol) of cesium fluoride under an argon gas flow, and
After stirring for an hour, 0.016 ml (0.185 ml) of ethylene bromide
mmol), d=2.172), and heated at 110 to 120℃ for 2 hours.
Stir for an hour. After the reaction is completed, the reaction mixture is diluted with chloroform to remove the cesium fluoride. Wash the liquid with 5% sodium hydroxide solution,
After drying over anhydrous sodium carbonate, the solvent is distilled off to obtain 77.4 mg of a brown residue.
これをアルミナカラムクロマトグラフイ
（Woelm.basic grade ８ｇ）を用い、ベン
ゼン―酢酸エチル（10：１）混液で溶出して留去
すると、無色の粉末26.8mg（収率26.3％）が得ら
れる。これをクロロホルム―アセトン混液から再
結晶すると、融点140〜142℃の目的化合物が無色
無晶性粉末として18.0mg（収率17.6％）得られ
る。 This is distilled off using alumina column chromatography (Woelm basic grade 8g) and eluted with a benzene-ethyl acetate (10:1) mixture to obtain 26.8 mg (yield 26.3%) of a colorless powder. When this is recrystallized from a chloroform-acetone mixture, 18.0 mg (yield 17.6%) of the target compound with a melting point of 140-142°C is obtained as a colorless amorphous powder.
NMR値：δ（CDCl3） 2.10〜3.77（13H、ｍ、脂肪族Ｈ） 2.57、2.61（each 3H、ｓNCH3 ×２） 3.69、3.93（each 3H、ｓ、−OCH3 ×２） 3.77〜4.03（2H、ｍ、−OCH2 CH2O―） 4.03〜4.33（3H、ｍ、１位又は1′位のＨ及び （−OCH2CH2 Ｏ―） 5.44（1H、ｓ、8′位のＨ） 6.23〜7.15（8H、ｍ、芳香環Ｈ） 7.41（1H、ｄ、Ｊ＝8.5Hz、芳香環Ｈ） IR値：νCHCl3 naxcm-1：特徴的なピークなし MS ｍ／ｅ： 622（M+＋２、9.6％） 621（M+＋１、41.3％） 620（M+、基準ピーク） 619（M+−１、75.2％） 以下の式は推定構造を示す。 NMR value: δ (CDCl 3 ) 2.10-3.77 (13H, m, aliphatic H) 2.57, 2.61 (each 3H, sNC H 3 ×2) 3.69, 3.93 (each 3H, s, −OC H 3 ×2) 3.77 ~4.03 (2H, m, -OC H 2 CH 2 O-) 4.03 ~ 4.33 (3H, m, H at position 1 or 1' and (-OCH 2 CH 2 O-) 5.44 (1H, s, 8 H at position ′) 6.23-7.15 (8H, m, aromatic ring H) 7.41 (1H, d, J = 8.5Hz, aromatic ring H) IR value: ν CHCl3 nax cm -1 : No characteristic peak MS m/ e: 622 (M + +2, 9.6%) 621 (M + +1, 41.3%) 620 (M + , reference peak) 619 (M + -1, 75.2%) The following formulas show the estimated structure.
元素分析値：C38H40N2O6：１／2CHCl3・１／
2H2Oとして
計算値（％） 67.07 6.07 4.06
実測値（％） 67.12 6.02 3.91
実施例 ３
デメチレンセフアランチン520mgを無水ジメチ
ルホルムアミド3.8mlに溶解する。この溶液をア
ルゴンガス気流中で弗化セシウム90mlに加え、室
温で１時間撹拌したのち１，３―二臭化プロパン
200mgを加え、120℃で16時間撹拌する。反応混合
物を氷水20mlに懸濁したのち、エーテル20mlで３
回抽出する。エーテル層を1N水酸化ナトリウム
溶液及び飽和食塩水で洗浄したのち、溶媒を減圧
留去する。残留物をシリカゲルクロマト〔ヘキサ
ン―酢酸エチル―ジエチルアミン（70：30：
0.5）〕で精製し、エーテル―酢酸エチル混液から
再結晶すると、融点142〜144℃の目的化合物が無
色無晶性粉末として5.2mg得られる。 Elemental analysis value: C 38 H 40 N 2 O 6 : 1/2 CHCl 3・1/
Calculated value (%) as 2H 2 O 67.07 6.07 4.06 Actual value (%) 67.12 6.02 3.91 Example 3 520 mg of demethylene cephalanthine is dissolved in 3.8 ml of anhydrous dimethylformamide. This solution was added to 90 ml of cesium fluoride in an argon gas stream, stirred at room temperature for 1 hour, and then added to 1,3-dibromide propane.
Add 200 mg and stir at 120°C for 16 hours. The reaction mixture was suspended in 20 ml of ice water, and then diluted with 20 ml of ether.
Extract times. After washing the ether layer with 1N sodium hydroxide solution and saturated brine, the solvent was distilled off under reduced pressure. The residue was chromatographed on silica gel [hexane-ethyl acetate-diethylamine (70:30:
0.5)] and recrystallized from an ether-ethyl acetate mixture to obtain 5.2 mg of the target compound as a colorless amorphous powder with a melting point of 142-144°C.
IR値：特徴的なピークなし MS ｍ／ｅ： 636（M+＋２） 4.1％ 635（M+＋１） 18.3％ 634（M+） 50.1％ 633（M+−１） 44.0％ 408 21.8％ 407 79.4％ 393 47.0％ 204（Base） 100.0％IR value: No characteristic peak MS m/e: 636 (M + +2) 4.1% 635 (M + +1) 18.3% 634 (M + ) 50.1% 633 (M + -1) 44.0% 408 21.8% 407 79.4 % 393 47.0% 204 (Base) 100.0%
Claims (1)
わされる化合物を一般式 Ｘ―（CH2）o−Ｙ （式中Ｘ及びＹはハロゲン原子、ｎは１〜３の整
数を示す）で表わされる化合物と反応させること
を特徴とする、一般式 （式中R1及びR2は低級アルキル基、ｎは１〜３
の整数を示す）で表わされるセフアランチン又は
その類似化合物の製法。 ２ 無機弗化物の存在下にジメチルホルムアミド
中で反応させることを特徴とする、特許請求の範
囲第１項に記載の方法。[Claims] 1. General formula (In the formula, R 1 and R 2 represent a lower alkyl group .) A compound represented by the general formula ) is characterized by reacting with a compound represented by the general formula (In the formula, R 1 and R 2 are lower alkyl groups, n is 1 to 3
A method for producing cephalantin or a similar compound thereof, represented by the following integer: 2. The method according to claim 1, characterized in that the reaction is carried out in dimethylformamide in the presence of an inorganic fluoride.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3964481A JPS57156491A (en) | 1981-03-20 | 1981-03-20 | Preparation of cepharanthine and analog thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3964481A JPS57156491A (en) | 1981-03-20 | 1981-03-20 | Preparation of cepharanthine and analog thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57156491A JPS57156491A (en) | 1982-09-27 |
| JPH0212233B2 true JPH0212233B2 (en) | 1990-03-19 |
Family
ID=12558787
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3964481A Granted JPS57156491A (en) | 1981-03-20 | 1981-03-20 | Preparation of cepharanthine and analog thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57156491A (en) |
-
1981
- 1981-03-20 JP JP3964481A patent/JPS57156491A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57156491A (en) | 1982-09-27 |
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