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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
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CAS No. : | 623-57-4 |
Formula : | C5H13NO2 |
M.W : | 119.16 |
SMILES Code : | OCC(O)CN(C)C |
MDL No. : | MFCD00004714 |
InChI Key : | QCMHUGYTOGXZIW-UHFFFAOYSA-N |
Pubchem ID : | 79078 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H314 |
Precautionary Statements: | P501-P280-P303+P361+P353-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310 |
Class: | 8 |
UN#: | 3267 |
Packing Group: | Ⅱ |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
> 90% | In ethanol; at 70℃; | EXAMPLE 1 Synthesis of Bis-(2.3-dihydroxypropyl)dimethylammonium Chloride General Procedure: Dimethylaminopropanediol (20 g, 0.168 moles) and 3-Chloropropane-1,2-diol (18.5 g, 0.168 moles) were stirred in ethanol (40 mL) at 70° C. until the reaction is complete. The reaction was monitored by LCMS. Upon completion, the reaction was allowed to cool and the solution was poured to a mixture of acetone:methyl-tert-butyl ether (2:1, 300 mL) to oil out the product. The Supernatant was decanted and product was washed with a mixture of acetone/methyl-tert-butyl ether (2*300 mL). The oil obtained was dried over high vacuum followed by freeze drying to obtain colorless oil/semisolid (>90percent yield). The pure product was characterized using 1H NMR, 13C NMR, and MS. Details on characterization as follows. |
> 90% | In ethanol; at 70℃; | EXAMPLE 10 Synthesis of Bis-(2.3-dihydroxypropyl)dimethylammonium Chloride General Procedure: Dimethylaminopropanediol (20 g, 0.168 moles) and 3-Chloropropane-1,2-diol (18.5 g, 0.168 moles) were stirred in ethanol (40 mL) at 70° C. until the reaction is complete. The reaction was monitored by LCMS. Upon completion, the reaction was allowed to cool and the solution was poured to a mixture of acetone:methyl-tert-butyl ether (2:1, 300 mL) to oil out the product. The Supernatant was decanted and product was washed with a mixture of acetone/methyl-tert-butyl ether (2*300 mL). The oil obtained was dried over high vacuum followed by freeze drying to obtain colorless oil/semisolid (>90percent yield). The pure product was characterized using 1H NMR, 13C NMR, and MS. Details on characterization as follows. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In dichloromethane; at 20℃; for 1h; | To 1 mol of <strong>[623-57-4]3-(dimethylamino)-1,2-propanediol</strong> 20 (1.2 g) dissolved in CH2Cl2 (5 mL), MeI (2 g, 1.5 mol) was added and the mixture stirred at rt for 1 h. The solution was then filtered and the filtrated recristalise in MeOH/Ether and dried in vacuo. (yield 100percent). The characterization data were consistent with the proposed structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
l g of N,N-dimethylamino-l ,2-propanediol (8.3 mmoles) and 2.2 molar equivalent of alkyl acid chain were dissolved in methylene chloride while stirring at room temperature. Then, 0.1 g DMAP and 2.2 molar equivalent of DCC were added and the solution was stirred for 3-4 hours or until complete by TLC. Additional small portions of DCC were added if necessary to drive the reaction to completion. The solution was then filtered to remove the precipitated DCU and washed 2X with 1M HCl. The organic layer was collected and dried with sodium sulfate and solvent was removed by rotary evaporation. The di-substituted dimethylaminoglycerol product (1) was moved forward with no further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88.9% | 2.41 kg of Nu,Nu'-carbonyldiimidazole is dissolved at room temperature in 6.33 kg of dry acetonitrile. The resultant solution is heated to 25°C. Then 4.0 kg of oleic acid is pumped into the solution over a period of 60 minutes while the reaction temperature is regulated below 35°C by the variation of the addition speed (formation of carbon dioxide gas). After the addition is completed the reaction solution is stirred for additional 90 minutes at 30°C (gas evolution ended). Then 11 g of 1 ,8-diazabicyclo[5.4.0]undec-7-ene is added followed by a solution of 0.83 kg of racemic (R,S)-3-(dimethylamino)- 1 ,2-propanediol in 0.37 kg of dry acetonitrile. Stirring at 30°C is continued for 21 hours. The resultant emulsion is cooled to 25°C and stirring is stopped. Two layers appear. The lower layer is isolated, degassed at 1 mbar/25°C for 200 minutes and finally diluted with 11.7 kg n-heptane. To the solution is added 1.21 kg of basic aluminium oxide and the suspension is stirred for 3 hours at 0°C. The suspension is filtered and the filter residue is washed with 1.5 kg of n-heptane previously cooled down to 0°C. The combined filtrates are homogenized to yield 15.9 kg solution of 4.08 kg pure (2R,S)-DODAP in n-heptane (lot no. MBA-116, assay: 25.7percent, yield:88.9percent). | |
11.12 g | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; at 20 - 30℃; for 1h; | <strong>[623-57-4]3-(dimethylamino)-1,2-propanediol</strong> 2.00 g (16.78 mmol, manufactured by Tokyo Chemical Industry Co., Ltd.), Oleic acid 9.48 g (33.56 mmol, Nisshin Oil Co., Ltd. "EXTRA OLEIN 99"), 4-dimethylaminopyridine 0.41 g (3.36 mmol, product of Koei Chemical Industry Co., Ltd.) was dissolved in 120 g of chloroform. There, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride 7.72 g (40.27 mmol, product of Tokyo Chemical Industry Co., Ltd.) And the mixture was stirred at 20 to 30 ° C. After 1 hour, it was washed with 120 g of ion exchange water and 120 g of 25 wtpercent saline, and 3.0 g of anhydrous magnesium sulfate was added to the organic layer and stirred. The magnesium sulfate was filtered off, The filtrate was desolvated with an evaporator to obtain DODAP (yield: 11.12 g, 17.16 mmol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 48h; | Dodecanedioic acid benzyl ester 2-(11-benzyloxycarbonyl-undecanoyloxy)-3-dimethylamino-propyl ester (29a) To an ice-cold solution of 24a (1.78 g, 5.5 mmol), 3-dimethylamino-propane-1,2-diol (0.3 mL, 2.5 mmol) and DMAP (catalytic amount) in DCM (15 mL) was slowly added a solution of DCC (1.1 g, 5.5 mmol) in DCM (5 mL). After the addition, the solution was warmed to room temperature and stirred for 2 days. The reaction mixture was then filtered to remove the insoluble DCU. Concentration of the filtrate followed by chromatography (50percent EtOAc/DCM to 100percent EtOAC) afforded 0.9 g (50percent yield) product as colorless oil. The characterization data were consistent with the proposed structure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 48h; | Dodecanedioic acid 2-(11-tert-butoxycarbonyl-undecanoyloxy)-3-dimethylamino-propyl ester tert-butyl ester (33) To an ice-cold solution of 26 (4.6 g, 16 mmol), 3-dimethylamino-propane-1,2-diol (0.9 mL, 7.6 mmol) and DMAP (catalytic amount) in DCM (40 mL) was slowly added a solution of DCC (4 g, 20 mmol) in DCM (10 mL). After the addition, the solution was warmed to room temperature and stirred for 2 days. The reaction mixture was then filtered to remove the insoluble DCU. Concentration of the filtrate followed by chromatography (50percent EtOAc/DCM to 100percent EtOAC) afforded 2.3 g (46percent yield) product as colorless oil. The characterization data were consistent with the chemical structure and formula. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | General procedure: Sodium hydride (38.6 mmol, 1.54 g, 60percent in oil) was charged in a 250 mL two-neck RB flask under nitrogen atmosphere and anhydrous THF (20 mL) was added to remove oil. The resulting suspension was stirred for 10 minutes and then the stirring was stopped to settle the sodium hydride solids. The supernatant liquid was removed with syringe and a fresh THF (100 mL) was added. To this slurry, a solution of 3-(dimethylamino)-propane-1,2-diol (14.9 mmol, 1.77 g) in THF (15 mL) was added dropwise for 10 minutes at RT. The resulting suspension was heated to reflux for 24 h. Then, a solution of methanesulfonic acid dodecyl ester (38.6 mmol, 10.2 g) in THF (22 mL) was added and again the mixture was heated to reflux for 5 days. Then, it was cooled to RT and the mixture was filtered through a 3-cm plug of celite while washing with ethyl acetate (1.0 L). The filtrate was removed under vacuum and the residue was partitioned between diethyl ether (250 mL) and 0.2M aqueous sodium hydroxide solution (250 mL). The two layers were separated and the organic layer was washed with water (200 mL), brine solution (200 mL), and dried over anhydrous magnesium sulfate. Filtration and concentration gave the light brown oil (7.93 g) which was purified using an ISCO (150 g) flash column chromatography to obtain 4.51 g (67percent yield) of (rac)-2,3-bis(dodecyloxy-propyl)-N,N-dimethyl-amine as a light yellow oil. ES(+)-HRMS m/e calcd. for C29H61NO2 (M+H)+ 456.4775, obsd. 456.4785. |