* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With sulfuric acid; acetic acid In ethanol at 70℃; for 3 h; Reflux; Large scale
in 500l of reaction kettle sequentially added 200 L of anhydrous ethanol, Reaction raw material vincamine 50 kg, Catalyst Sodium ethoxide 3.0 kg then keep the system pH at about 14 and slowly raised temperature to 70 ° C and allow to react for 3 h. Thin layer chromatography monitoring of raw materials vincamine fully reacted. As the hydrolysis reaction is completed, the product is vincamine acid and dehydrated vincamine mixture. Continue in the same reactor, stirring and cooling below 10 ° C, adjusting ph to about 12 by adding glacial acetic acid then again raise the temperature to reflux and allowed to react for 2h. TLC analysis of vincamine acid point of not more than 5percent, as dehydration reaction is completed. Obtained a product of dehydrating vincamine acid. Continue in the same reactor, stirring down 10 ° C below then the addition of acetic anhydride 14.5 and the reaction of water was generated. Then added acetic acid to adjust pH , stirred the reaction for 1h and system pH value was about 7. Then add concentrated sulfuric acid to adjust the pH value to about 2, and then heated to 65-75 ° C and allowed to react for 6-8 h. TLC analysis of raw materials dehydrated vincamine acid intermediate reaction completed and completed as ethyl esterification reaction. The reaction system was stirred and cooled below 10 ° C, adjust the pH to about 7 by adding 30percent of sodium hydroxide solution as vinpocetine synthesis steps to complete.. The synthesis step of vincristine ethanol solution into the concentrator, concentrated under reduced pressure recovery of ethanol. Then add 200L methylene chloride and 200L water, into the extraction tank for extraction and separation, dichloromethane extraction separation twice, the organic phase, dried with anhydrous sodium sulfate. And then transferred to the mixer with a mixer to recover dichloromethane to dry, get vinca cis-crude. Then add 450L of anhydrous ethanol to dissolve, fine filter, the filtrate into the crystallization tank with a concentrator. After evaporation of 300 L of ethanol under reduced pressure, the mixture was cooled to below 10 ° C for 2 h, filtered and dried to obtain 43.2 kg of vincristine and 86.4percent by weight. HPLC detection purity of 99.3percent, the external standard method measured content of 99.5percent.
With sodium ethanolate In tetrahydrofuran at -10 - -5℃;
Example 6 Oppolzer's aldehyde (10.0 g, 0.035 mol) was dissolved in THF (60 ml) - 5°C. Separately, sodium ethoxide (6.0 g, 0.088 mol) was dissolved in THF (40 ml). The two solutions were joined maintaining the temperature within the range of from -5° to -10°C. Then, ethyl chloroacetate (5.6 ml, 6.44 g, 0.052 mol) was added dropwise over 30 min, under stirring and controlling the temperature below -5°C. Before completion of the reaction, ethyl acetate (30 ml) is added and the temperature of the reaction mixture is raised to 50°C for two hours. Then, the reaction mixture was distilled under reduced pressure. The residual was added with water and dichloromethane. The organic phase was separated and subjected to chromatography on a silicon dioxide column using as eluent a mixture of 98percent dichloromethane and 2percent methanol. Pure vinpocetine was obtained (7.94 g) with a yield of 79.4percent w/w and 64.7percent m/m based on the starting aldehyde.
While stirring, 3.80 kg of aprichengchun amine and 46 L of anhydrous ethanol were put into a 100 L reaction kettle, Heated to ethanol reflux, until the material is basically clear, Then add ethanol sodium ethanol solution 1.45L, The reaction was stirred at reflux for 1 hour. The sample was monitored by HPLC and the reflux was stopped when the starting apache amine content was 0.659percent (less than 3percent). With tap water cooled to about 40 , all solvents were removed under reduced pressure to obtain solid, and then re-added 46L of fresh ethanol, and then heated to reflux until clear, ethanol solution of sodium ethoxide 0.35L, and then refluxed reaction 30 minute. Re-monitoring, when the raw material apricot amine content less than 0.3percent immediately end the reaction. Add ethanol 40-60L, reflux and clear. With preheated to 60-70 D40 stainless steel porous quick filter hot filtered reaction solution to remove insoluble. The filtrate was transferred to a clean and dry 100L reactor, the material will precipitate, and then defrost after steamed some of the ethanol, control the remaining amount of ethanol in the reactor 35-43L. Under stirring, after about 10-12 hours of natural cooling to cool down to near normal temperature, and then open the jacket tap water and continue stirring for 2 hours aging crystallization. The material was drained, drained, and thoroughly rinsed with 6L × 2 portions of absolute ethanol, drained and dried to collect the filter cake, which was crude vinpocetine
Reference：
[1] Liebigs Annalen der Chemie, 1993, # 3, p. 221 - 230
[2] Patent: CN106632310, 2017, A, . Location in patent: Paragraph 0018; 0141; 0147-0153
In ethanol; for 1.0h;Reflux; Autoclave; Industrial scale;
While stirring, 3.80 kg of aprichengchun amine and 46 L of anhydrous ethanol were put into a 100 L reaction kettle, Heated to ethanol reflux, until the material is basically clear, Then add ethanol sodium ethanol solution 1.45L, The reaction was stirred at reflux for 1 hour. The sample was monitored by HPLC and the reflux was stopped when the starting apache amine content was 0.659% (less than 3%). With tap water cooled to about 40 , all solvents were removed under reduced pressure to obtain solid, and then re-added 46L of fresh ethanol, and then heated to reflux until clear, ethanol solution of sodium ethoxide 0.35L, and then refluxed reaction 30 minute. Re-monitoring, when the raw material apricot amine content less than 0.3% immediately end the reaction. Add ethanol 40-60L, reflux and clear. With preheated to 60-70 D40 stainless steel porous quick filter hot filtered reaction solution to remove insoluble. The filtrate was transferred to a clean and dry 100L reactor, the material will precipitate, and then defrost after steamed some of the ethanol, control the remaining amount of ethanol in the reactor 35-43L. Under stirring, after about 10-12 hours of natural cooling to cool down to near normal temperature, and then open the jacket tap water and continue stirring for 2 hours aging crystallization. The material was drained, drained, and thoroughly rinsed with 6L × 2 portions of absolute ethanol, drained and dried to collect the filter cake, which was crude vinpocetine
(11aS,11bS)-11a-Ethyl-8-[2-(1H-indol-3-yl)-ethylsulfamoyl]-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-7-[2-(1H-indol-3-yl)-ethylsulfamoyl]-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-8-(4-methoxy-phenylsulfamoyl)-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-7-(4-methoxy-phenylsulfamoyl)-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-8-[2-(4-methoxy-phenyl)-ethylsulfamoyl]-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-7-[2-(4-methoxy-phenyl)-ethylsulfamoyl]-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-8-(4-Cyano-phenylsulfamoyl)-11a-ethyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-7-(4-Cyano-phenylsulfamoyl)-11a-ethyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-8-[2-(2-methoxy-phenyl)-ethylsulfamoyl]-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-7-[2-(2-methoxy-phenyl)-ethylsulfamoyl]-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-8-(1,2-Diphenyl-ethylsulfamoyl)-11a-ethyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-7-(1,2-Diphenyl-ethylsulfamoyl)-11a-ethyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-8-(1-methoxycarbonyl-3-methylsulfanyl-propylsulfamoyl)-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-7-(1-methoxycarbonyl-3-methylsulfanyl-propylsulfamoyl)-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(i) Synthesis of ethyl apovincaminate Vincaminic acid (6.0 g) was added to 180 ml of ethanol. After 34.5 g (352 mmol) of concentrated sulfuric acid were carefully added under stirring over ice bath, the resultant mixture was heated under reflux for 8 hours. The reaction mixture was concentrated under reduced pressure, followed by the addition of 100 ml of ice water. The thus-obtained mixture was neutralized with a 10% aqueous solution of NaOH. Precipitated crystals were extracted with dichloromethane (50 ml x 3). The extracts were washed with a saturated aqueous solution of NaCl and then dried over magnesium sulfate. The solvent was distilled off under reduced pressure. Ethanol was added to the residue to induce crystallization. Crystals were collected by filtration, whereby 4.9 g of the title compound were obtained (yield: 79%). 1H-NMR(270MHz,CDCl3)delta(ppm): 7.46(1H,d,J=8.6Hz), 7.24(1H,d,J=8.6Hz), 7.18-7.08(2H,m), 6.11(1H,s), 4.47-4.38(2H,m), 4.14(1H,brs), 3.35(1H,dd,J=13.7,5.4Hz), 3.25(1H,ddd,J=13.5,11.2,5.0Hz), 3.09-2.93(1H,m), 2.62(2H,dd,J=8.7,2.8Hz), 2.50(1H,brd,J=16.3Hz), 1.91(2H,m), 1.76-1.63(1H,m), 1.51(1H,brd,J=13.5Hz), 1.43-1.32(1H,m), 1.39(3H,t,J=7.3Hz), 1.01(3H,t,J=7.6Hz), 1.06-0.91(1H,m).
To a solution of the crude oil of 16-ethoxycarbonyl-17-hydroxyeburnane obtained above in 50 ml of toluene was added in portions 0.3 g of sodium hydride (65%) at room temperature. After refluxing for 30 minutes, the reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous sodium sulfate, concentrated under reduced pressure and chromatographed on silica gel to give ethyl apovincaminate IR nucm-1;film: 1720 cm-1 NMR delta(CDCl3): 1.0 ppm, 1.35, 4.48, 6.18.
2.5 g (4.5 mmols) of the compound obtained above, in 75 ml of formic acid, are heated to the reflux temperature and 60 ml of 15% strength solution of titanium (III) chloride are added. The reaction mixture is heated for 20 minutes under reflux and ice is then added. The titanium dioxide is removed by filtration and the product is extracted with methylene chloride. The organic phases are washed with ammonia solution and then with water and are then dried over sodium sulphate. The solvent is removed and the solid residue is recrystallized from petroleum ether. This yields 1.24 g of ethyl apovincaminate in the form of a pale yellow solid. Melting point=122 C.
From the elude of the column the following products are serially recovered: (1) ethyl apovincaminate (2) ethyl vincaminate (3) ethyl epivincaminate (4) vincanol (I:R=OH, R'=R"=OH).
In a further embodiment, compounds that are useful for the sodium ion channel blocker or a pharmaceutically acceptable salt or prodrug thereof in connection with the present invention, the structures for which are set forth in Table 3C below, include, but are not limited to: ... 2-amino-6-(trifluoromethoxy) benzothiazole (C-9); Octahydro-12-(hydroxymethyl)-2-imino-5,9,7,10 a-dimethano-10 aH-[1,3]dioxocino[6,5-d]pyrimidine-4,7,10,11,12-pentol (C-10); Vinpocetine (C-11); (E)-1-[bis(4-fluorophenyl)methyl]-4-(3-phenyl-2-propenyl)piperazine (C-12); ...
28
[ 42971-09-5 ]
[ 27773-65-5 ]
Yield
Reaction Conditions
Operation in experiment
98%
With sodium hydroxide; In 1,4-dioxane; at 80℃; for 2.0h;
To a mixture of sodium hydroxide (137 mg, 3.43 mmol) and anhydrous dioxane (14 mL) was added <strong>[42971-09-5]vinpocetin</strong>e (1 g, 2.86 mmol) at 80 C., and the mixture was reacted at such temperature for 2 hours. After <strong>[42971-09-5]vinpocetin</strong>e was consumed (monitored by TLC), the mixture was concentrated to dry, water was added to dissolve the residue, the pH of the solution obtained was adjusted to 3 with 2M hydrochloric acid. The mixture was extracted with a mixed solution of dichloromethane/isopropanol (10/1 by volume), the extract was dried and concentrated to obtain the target compound (for the next step, 900 mg, yield: 98%). LCMS (ESI) m/z: 323 (M+1)
92.4%
With sodium hydroxide; In ethanol; for 5.0h;Reflux;
A mixture of 20 g (57.0 mmol) of (3aS,l lbS)-3a-ethyl-l,2,3,3a,10,l lb-hexahydro-11H- 5a, 1 la-diaza-benzo[cd]fluoranthene-5-carboxylic acid ethyl ester and 3.0 g (75.0 mmol) of sodium hydroxide in 120 mL of ethanol was re fluxed for 5 h. The reaction mixture was cooled, concentrated in vacuo and the residue was dissolved in 200 mL of water. The solution was acidified with 12 mL of acetic acide. The precipitated product was filtered off, washed with water and dried to yield 17.0 g (92.4 %) of the title compound. Mp: 257-259 C. MS (EI) 323.1 (MH+).
(11aS,11bS)-11a-Ethyl-7-(4-methyl-piperazine-1-sulfonyl)-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-7-(naphthalen-1-ylsulfamoyl)-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-7-(2-methoxy-ethylsulfamoyl)-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-7-[ethyl-(2-hydroxy-ethyl)-sulfamoyl]-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-7-(piperidine-1-sulfonyl)-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-7-(2-Dimethylamino-ethylsulfamoyl)-11a-ethyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-7-(morpholine-4-sulfonyl)-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-7-(1-phenyl-ethylsulfamoyl)-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-7-(Ethoxycarbonylmethyl-sulfamoyl)-11a-ethyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-7-(3-methoxycarbonyl-propylsulfamoyl)-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-11a-Ethyl-7-(2,4,6-trimethyl-phenylsulfamoyl)-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS)-7-[2-(3,4-Dimethoxy-phenyl)-ethylsulfamoyl]-11a-ethyl-2,3,4,5,11a,11b-hexahydro-1H-3a,9b-diaza-benzo[cd]fluoranthene-10-carboxylic acid ethyl ester[ No CAS ]
(11aS,11bS,11'aS,11'bS)-11a,11'a-Diethyl-4,5,11a,11b,2',3',4',5',11'a,11'b-decahydro-1H,1'H-[2,3']bi[3a,9b-diaza-benzo[cd]fluoranthenyl]-10,10'-dicarboxylic acid diethyl ester[ No CAS ]
(1R,5S,12bS)-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-1-carbaldehyde[ No CAS ]
[ 105-39-5 ]
[ 42971-09-5 ]
Yield
Reaction Conditions
Operation in experiment
79.4%
With sodium ethanolate; In tetrahydrofuran; at -10 - -5℃;Product distribution / selectivity;
Example 6 Oppolzer's aldehyde (10.0 g, 0.035 mol) was dissolved in THF (60 ml) - 5C. Separately, sodium ethoxide (6.0 g, 0.088 mol) was dissolved in THF (40 ml). The two solutions were joined maintaining the temperature within the range of from -5 to -10C. Then, ethyl chloroacetate (5.6 ml, 6.44 g, 0.052 mol) was added dropwise over 30 min, under stirring and controlling the temperature below -5C. Before completion of the reaction, ethyl acetate (30 ml) is added and the temperature of the reaction mixture is raised to 50C for two hours. Then, the reaction mixture was distilled under reduced pressure. The residual was added with water and dichloromethane. The organic phase was separated and subjected to chromatography on a silicon dioxide column using as eluent a mixture of 98% dichloromethane and 2% methanol. Pure vinpocetine was obtained (7.94 g) with a yield of 79.4% w/w and 64.7% m/m based on the starting aldehyde.
With sulfuric acid; acetic acid; In ethanol; at 70℃; for 3.0h;pH 2 - 14;Reflux; Large scale;
in 500l of reaction kettle sequentially added 200 L of anhydrous ethanol, Reaction raw material vincamine 50 kg, Catalyst Sodium ethoxide 3.0 kg then keep the system pH at about 14 and slowly raised temperature to 70 C and allow to react for 3 h. Thin layer chromatography monitoring of raw materials vincamine fully reacted. As the hydrolysis reaction is completed, the product is vincamine acid and dehydrated vincamine mixture. Continue in the same reactor, stirring and cooling below 10 C, adjusting ph to about 12 by adding glacial acetic acid then again raise the temperature to reflux and allowed to react for 2h. TLC analysis of vincamine acid point of not more than 5%, as dehydration reaction is completed. Obtained a product of dehydrating vincamine acid. Continue in the same reactor, stirring down 10 C below then the addition of acetic anhydride 14.5 and the reaction of water was generated. Then added acetic acid to adjust pH , stirred the reaction for 1h and system pH value was about 7. Then add concentrated sulfuric acid to adjust the pH value to about 2, and then heated to 65-75 C and allowed to react for 6-8 h. TLC analysis of raw materials dehydrated vincamine acid intermediate reaction completed and completed as ethyl esterification reaction. The reaction system was stirred and cooled below 10 C, adjust the pH to about 7 by adding 30% of sodium hydroxide solution as vinpocetine synthesis steps to complete.. The synthesis step of vincristine ethanol solution into the concentrator, concentrated under reduced pressure recovery of ethanol. Then add 200L methylene chloride and 200L water, into the extraction tank for extraction and separation, dichloromethane extraction separation twice, the organic phase, dried with anhydrous sodium sulfate. And then transferred to the mixer with a mixer to recover dichloromethane to dry, get vinca cis-crude. Then add 450L of anhydrous ethanol to dissolve, fine filter, the filtrate into the crystallization tank with a concentrator. After evaporation of 300 L of ethanol under reduced pressure, the mixture was cooled to below 10 C for 2 h, filtered and dried to obtain 43.2 kg of vincristine and 86.4% by weight. HPLC detection purity of 99.3%, the external standard method measured content of 99.5%.
With perchloric acid; In methanol; water; at 20 - 40℃; for 1.33h;
At room temperature, <strong>[42971-09-5]vinpocetin</strong>e (350 mg, 1 mmol) was added to a 100 ml Erlenmeyer flask,80 ml of a mixed solvent of methanol and water (4: 1) was added and the mixture was stirred for 1 hour with a magnetic carrier. The solution was clarified,Dropping 1 mmol of perchloric acid, stirring for 20 minutes, the solid slowly precipitated, and then raised the temperature of 40 ,Solid without melting, and then slowly add perchloric acid, when adding about 3mmol, the solid dissolved,After 40 degrees under the slow evaporation, when the solid, the filter, with a small amount of methanol washing, the new salt crystal.
<strong>[42971-09-5]Vinpocetine</strong> (350 mg, 1 mmol) and D-tartaric acid (150 mg, 1 mmol) were added to a 50 ml Erlenmeyer flask at 0 C,Add 20ml of methanol, add in batches, when the solution has a slight turbidity, stop adding, stirring hours, directly heated to 40 C, a large number of solid precipitation, filtration drying, the product.
<strong>[42971-09-5]Vinpocetine</strong> (350 mg, 1 mmol) and L-tartaric acid (150 mg, 1 mmol) were added to a 10 ml Erlenmeyer flask at 0 C, 2 ml of methanol were added, added in portions, When the amount of solution added is greater than the valence of <strong>[42971-09-5]vinpocetin</strong>e 92.1mg / ml solubility, Stop adding, stirring hours, directly heated to 40 , Maintain the temperature and slowly evaporate until the solution evaporates
4-((41S,13aS)-13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12-yl)heptan-4-ol[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In tetrahydrofuran; at 0℃; for 4.0h;Inert atmosphere;
n-propylmagnesium bromide (2M in tetrahydrofuran, 2.14 mL, 4.29 mmol) was slowly added dropwise to a solution of <strong>[42971-09-5]vinpocetin</strong>e (300 mg, 0.86 mmol) in tetrahydrofuran (2 mL) at 0 C. under an atmosphere of nitrogen, then the mixture was stirred for another 4 hours under such condition. Saturated ammonium chloride solution (20 mL) was added into the mixture, and the mixture was extracted with 40 mL ethyl acetate. The extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by Preparative High Performance Liquid Chromatography to obtain the target compound. 1H NMR (400 MHz, MeOD) delta ppm 8.51-8.63 (m, 1H), 7.34-7.44 (m, 1H), 7.00-7.14 (m, 2H), 5.30 (s, 1H), 4.09 (br. s., 1H), 3.20-3.31 (m, 2H), 2.99-3.13 (m, 1H), 2.52-2.71 (m, 3H), 1.95 (br. s., 4H), 1.43 (br. s., 8H), 0.96-1.14 (m, 8H), 0.72 (t, J=7.28 Hz, 3H). LCMS (ESI) m/z: 393 (M+1)
ethyl (S)-methyl-2-((4S,13aS)-13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12-formylamino)propionate[ No CAS ]
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