Purity | Size | Price | VIP Price | USA Stock *0-1 Day | Global Stock *5-7 Days | Quantity | |||||
{[ item.p_purity ]} | {[ item.pr_size ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} |
{[ getRatePrice(item.pr_usd, 1,1) ]} | Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]} | {[ item.pr_usastock ]} | Inquiry - | {[ item.pr_chinastock ]} | Inquiry - |
* Storage: {[proInfo.prStorage]}
CAS No. : | 15809-19-5 | MDL No. : | MFCD27964769 |
Formula : | C26H47ClN2O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JQQZCIIDNVIQKO-UHFFFAOYSA-N |
M.W : | 439.12 | Pubchem ID : | 72949 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
In ethanol; at 78℃;Reflux; | General procedure: The prepared N-(3-(dimethylamino) propyl) alkanamide (0.1 mol) from the previous step was refluxed with benzyl chloride (0.1 mol) in 150 ml ethanol at 78 C from 25 to 30 h depending on the alkyl chain length of the amide(shorter chain length requires less time). The solvent was evaporated under vacuum and the residue subject to recrystallization using diethyl ether. The reaction yield was 97-98 % for the three synthesized products. The obtained amido-cationic surfactants were named C12Bn, C14Bn and C16Bn and the general procedure for the synthesis is depicted in Scheme 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 137 °C / Dean-Stark 2: ethanol / 78 °C / Reflux | ||
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / 5,5-dimethyl-1,3-cyclohexadiene / 24 h / 137 °C 2: ethanol / 78 °C / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.2% | With hydrogen iodide In methanol; water | 4.b 4.b. General procedure for acids poorly soluble or insoluble in MeOH General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid (25 mmol) in H2O (20 ml) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange - preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
39.9% | With sodium nitrite In methanol; water | 4.d General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid salt (25 mmol) in H2O (20 ml) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange - preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.9% | With potassium bromide In methanol; water | 4.d General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid salt (25 mmol) in H2O (20 ml) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange - preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
557 mg | In water at 20℃; for 3h; | 1 Synthesis of Myramistin dodecylsulfate - 7 (ES001392) Myramistin chloride (500 mg, 1.14 mmol) was dissolved in 5 ml_ water at room temperature. After 2 minutes of sonication, SDS (sodium dodecylsulfate, 328 mg, 1.14 mmol) was added to the homogenous solution. The SDS seemed to dissolve, while a white solid with a different appearance seemed to precipitate. After 3 hours of stirring at room temperature, the precipitate is collected via filtration. No residual chloride is found and the precipitate is dried under reduced pressure to give Myramystine dodecylsulfate 7 (0.83 mmol, 557 mg). 1H NMR analysis shows the presence of both anion and cation, in equal proportions. 1H NMR analysis (DMSO-c/6): d 7.91 (1H, br t, J = 5.6 Hz), 7.60-7.43 (5H, m), 4.50 (2H, s), 3.66 (2H, t, J = 6.6 Hz), 3.21 (2H, m), 3.11 (2H, m), 2.94 (6H, s), 2.04 (2H, br t, J= 7.5 Hz), 1.93 (2H, m), 1.46 (4H, m), 1.38-1.12 (38H, m), 0.85 (6H, br t, J = 6.6 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.4% | Stage #1: acetic acid With Amberlyst A26 In methanol Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol | 4.a 4. a. General procedure for acids soluble in MeOH General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid (25 mmol) in MeOH (20 ml) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange - preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65.2% | Stage #1: ascorbic acid With Amberlyst A26 In methanol; water Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol; water | 4.b 4.b. General procedure for acids poorly soluble or insoluble in MeOH General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid (25 mmol) in H2O (20 ml) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange - preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75.9% | Stage #1: sodium hydrogencarbonate With Amberlyst A26 In methanol; water Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol; water | 4.b 4.b. General procedure for acids poorly soluble or insoluble in MeOH General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid (25 mmol) in H2O (20 ml) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange - preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81.7% | Stage #1: L-Tartaric acid With Amberlyst A26 In methanol; water Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol; water | 4.b 4.b. General procedure for acids poorly soluble or insoluble in MeOH General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid (25 mmol) in H2O (20 ml) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange - preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.7% | Stage #1: gluconic acid With Amberlyst A26 In methanol; water Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol; water | 4.b 4.b. General procedure for acids poorly soluble or insoluble in MeOH General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid (25 mmol) in H2O (20 ml) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange - preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83.7% | Stage #1: glycine With Amberlyst A26 In methanol; water Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol; water | 4.b 4.b. General procedure for acids poorly soluble or insoluble in MeOH General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid (25 mmol) in H2O (20 ml) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange - preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.4% | Stage #1: L-alanin With Amberlyst A26 In methanol; water Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol; water | 4.b 4.b. General procedure for acids poorly soluble or insoluble in MeOH General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid (25 mmol) in H2O (20 ml) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange - preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.1% | Stage #1: L-leucine With sodium hydroxide In methanol; water Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol; water | 4.c 4.c. General procedure for acids poorly soluble or insoluble in H2O General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid (27.5 mmol) in aqueous NaOH (1.25M, 20 ml, 25 mmol) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.2% | Stage #1: L-Tryptophan With sodium hydroxide In methanol; water Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol; water | 4.c 4.c. General procedure for acids poorly soluble or insoluble in H2O General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid (27.5 mmol) in aqueous NaOH (1.25M, 20 ml, 25 mmol) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.1% | Stage #1: L-Aspartic acid With sodium hydroxide In methanol; water Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol; water | 4.c 4.c. General procedure for acids poorly soluble or insoluble in H2O General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid (27.5 mmol) in aqueous NaOH (1.25M, 20 ml, 25 mmol) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | Stage #1: nicotinic acid With sodium hydroxide In methanol; water Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol; water | 4.c 4.c. General procedure for acids poorly soluble or insoluble in H2O General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid (27.5 mmol) in aqueous NaOH (1.25M, 20 ml, 25 mmol) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85.7% | Stage #1: saccharin With sodium hydroxide In methanol; water Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol; water | 4.c 4.c. General procedure for acids poorly soluble or insoluble in H2O General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid (27.5 mmol) in aqueous NaOH (1.25M, 20 ml, 25 mmol) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.2% | Stage #1: potassium acetate With Amberlyst A26 In methanol; water Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol; water | 4.d General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid salt (25 mmol) in H2O (20 ml) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange - preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.4% | Stage #1: sodium phenylsulfonate With Amberlyst A26 In methanol; water Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol; water | 4.d General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid salt (25 mmol) in H2O (20 ml) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange - preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72.1% | Stage #1: sodium D-gluconate With Amberlyst A26 In methanol; water Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol; water | 4.d General procedure: Conditioning of the ion exchange resin An empty SPE cartridge with bottom frit was filled with Amberlyst A26 ion exchange resin, hydroxide form (4 g)*, and a frit was placed on top of the resin. The resin was wetted with MeOH (5 ml). The flowthrough was discarded. A solution of the acid salt (25 mmol) in H2O (20 ml) was loaded on top of the ion exchange cartridge and allowed to slowly pass through the column. The flowthrough was discarded. Finally, the ion exchange resin was washed with MeOH (25 ml). The flowthrough was discarded. Ion exchange - preparation of the Myramistin salt Myramistin (200 mg, 0.455 mmol) was dissolved in MeOH (1.0 ml) and loaded on top of the conditioned ion exchange column. MeOH (5 ml) was used to elute the product. Both flowthroughs were combined and dried under a stream of N2. The residue was further dried under high vacuum to yield the Myramistin salt. * Amberlyst A 26 has > 0.8 meq/ml; 4.0 g*0.675 g/ml = 5.93 ml resin*0.8 meq/ml = 4.74 mmol, i.e., at least 10 eqs. vs. Myramistin; 25 mmol acid corresponds to approximately 5 eqs. vs. the ion exchange resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Stage #1: benzoic acid With Amberlyst A26 In methanol for 0.5h; Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol | 1 Synthesis of Myramistin benzoate - 3 (ES001388) For the synthesis of Myramistin benzoate, 2.5 g Amberlyst A26 anion exchange resin was conditioned with a solution of benzoic acid in methanol (1.221 g in 20 mL solvent) for a contact time of 30 minutes. Next, the resin was washed with methanol until the pH of the eluent was no longer acidic. Myramistin chloride (0.438 g, 1 mmol) was dissolved in 20 mL MeOH and brought on the resin. The eluent was collected in fractions and the presence of the Myramistin derivative was checked with TLC-UV. The solvent was evaporated under reduced pressure to give 0.515 g Myramistin benzoate 3 (0.98 mmol, 98% yield). 1H NMR analysis (DMSO-c/6): d 8.25 (1H, br t, J = 5.6 Hz), 7.86 (2H, m), 7.58-7.44 (5H, m), 7.39-7.25 (3H, m), 4.53 (2H, s), 3.27 (2H, m), 3.12 (2H, m), 2.95 (6H, s), 2.05 (2H, br t, J = 7.5 Hz), 1.94 (2H, m), 1.45 (2H, m), 1.32-1.11 (20H, m), 0.85 (3H, br t, J = 6.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In methanol at 20℃; for 2.5h; | 1 Synthesis of Myramistin salicylate - 2 (ES001387) Dissolve sodium salicylate (2.552 g, 15.9 mmol) in MeOH (14 mL) and sonicate for 1 min. Add Myramistin chloride (0.925 g, 15.9 mmol) and the solution becomes a suspension. After 2,5 h stirring at room temperature, the solvent was removed under reduced pressure and 50 mL acetone was added. The mixture was sonicated, heated at 45°C for 5 min and the solids were filtered and were washed with acetone. The filtrate was concentrated in vacuo to give 8.226 g Myramistin salicylate 2 (15.2 mmol, 95% yield). 1H NMR analysis (CDC): d 8.53 (1H, br t, J = 5.2 Hz), 7.96 (1H, dd, J = 1.8, 7.7 Hz), 7.56-7.39 (5H, m), 7.26 (1H, dt, J = 1.8, 7.2 Hz), 6.86 (1H, dd, J = 1.0, 8.2 Hz), 6.76 (1H, dt, J = 1.1, 7.6 Hz), 4.57 (2H, s), 3.92 (2H, m), 3.39 (2H, m), 3.02 (6H, s), 2.21 (2H, br t, J = 7.8 Hz), 2.11 (2H, m), 1.56 (2H, m), 1.35-1.15 (20H, m), 0.88 (3H, br t, J = 6.8 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | Stage #1: n-tetradecanoic acid With Amberlyst A26 In methanol for 0.5h; Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In methanol | 1 Synthesis of Myramistin myristate - 4 (ES001389) For the synthesis of Myramistin myristate, 2.5 g Amberlyst A26 anion exchange resin was conditioned with a solution of myristic acid in methanol (2.284 g in 20 mL solvent) for a contact time of 30 minutes. Next, the resin was washed with methanol (3 x 10 mL). pH neutrality could not be checked since the low solubilty of myristic acid in water. Myramistin chloride (0.438 g, 1 mmol) was dissolved in 20 mL MeOH and brought on the resin. The eluent was collected in fractions and the presence of the Myramistin derivative was checked with TLC-UV. The solvent was evaporated under reduced pressure to give 0.563 g Myramistin myristate 4 (0.89 mmol, 89% yield). 1H NMR analysis (CDaOD): d 7.63-7.49 (5H, m), 4.53 (2H, s), 3.36-3.24 (4H, m), 3.04 (6H, s), 2.23-2.01 (6H, m), 1.59 (4H, m), 1.38-1.22 (40H, m), 0.90 (6H, br t, J = 6.7 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | Stage #1: L-Lactic acid With Amberlyst A26 In water for 0.5h; Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In water | 1 Synthesis of Myramistin (L)-lactate - 6 (ES001391) For the synthesis of Myramistin (L)-lactate, 2.5 g Amberlyst A26 anion exchange resin was conditioned with an aqueous solution of (L)-lactic acid (901 mg, 20wt% in 20 mL solvent) for a contact time of 30 minutes. Next, the resin was washed with water until the pH of the eluent was no longer acidic. Myramistin chloride (0.438 g, 1 mmol) was dissolved in 20 mL water and brought on the resin. The eluent was collected in fractions and the presence of the Myramistin derivative was checked with TLC-UV. The mixture was lyophilized to give 0.485 g of Myramistin (L)-lactate 6 (0.99 mmol, 99% yield). 1H NMR analysis (DMSO-c/6): d 8.00 (1H, br t, J 6.0 Hz), 7.59-7.43 (5H, m), 4.51 (2H, s), 3.50 (1H, q, J = 6.7 Hz), 3.22 (2H, m), 3.12 (2H, m), 2.94 (6H, s), 2.04 (2H, br t, J = 7.5 Hz), 1.93 (2H, m), 1.46 (2H, m), 1.35-1.13 (20H, m), 1.07 (3H, d, J = 6.7 Hz), 0.85 (3H, br t, J = 6.7 Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | Stage #1: formic acid With Amberlyst A26 In water for 0.5h; Stage #2: benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride In water | 1 Synthesis of Myramistin formate - 5 (ES001390) For the synthesis of Myramistin formate, 2.5 g Amberlyst A26 anion exchange resin was conditioned with an aqueous solution of formic acid (460 mg in 20 mL solvent) for a contact time of 30 minutes. Next, the resin was washed with water until the pH of the eluent was no longer acidic. Myramistin chloride (0.438 g, 1 mmol) was dissolved in 20 mL water and brought on the resin. The eluent was collected in fractions and the presence of the Myramistin derivative was checked with TLC-UV. The mixture was lyophilized yielding 0.148 g of Myramistin formate 5 (0.33 mmol, 33% yield). 1H NMR analysis (DMSO-c/6): d 8.58 (1H, s), 8.36 (1H, br t, J = 5.6 Hz), 7.60-7.44 (5H, m), 4.53 (2H, s), 3.27 (2H, m), 3.11 (2H, m), 2.95 (6H, s), 2.05 (2H, t, J = 7.5 Hz), 1.94 (2H, m), 1.45 (2H, m), 1.33-1.11 (20H, m), 0.85 (3H, br t, J = 6.7 Hz). |