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[ CAS No. 15809-19-5 ] {[proInfo.proName]}

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Chemical Structure| 15809-19-5
Chemical Structure| 15809-19-5
Structure of 15809-19-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 15809-19-5 ]

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 :

Safety of [ 15809-19-5 ]

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:

Application In Synthesis of [ 15809-19-5 ]

* 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.

  • Downstream synthetic route of [ 15809-19-5 ]

[ 15809-19-5 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 45267-19-4 ]
  • [ 100-44-7 ]
  • benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 2
  • [ 544-63-8 ]
  • [ 109-55-7 ]
  • [ 15809-19-5 ]
YieldReaction ConditionsOperation 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
  • 3
  • [ 15809-19-5 ]
  • [ 2704606-01-7 ]
YieldReaction ConditionsOperation 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.
  • 4
  • [ 15809-19-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation 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.
  • 5
  • [ 15809-19-5 ]
  • [ 1813530-17-4 ]
YieldReaction ConditionsOperation 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.
  • 6
  • [ 15809-19-5 ]
  • [ CAS Unavailable ]
  • [ 2704605-82-1 ]
YieldReaction ConditionsOperation 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).
  • 7
  • [ 15809-19-5 ]
  • [ CAS Unavailable ]
  • [ 2704605-85-4 ]
YieldReaction ConditionsOperation 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.
  • 8
  • [ 15809-19-5 ]
  • [ 50-81-7 ]
  • [ 2803602-56-2 ]
YieldReaction ConditionsOperation 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.
  • 9
  • [ 15809-19-5 ]
  • [ CAS Unavailable ]
  • [ 2704606-04-0 ]
YieldReaction ConditionsOperation 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.
  • 10
  • [ 87-69-4 ]
  • [ 15809-19-5 ]
  • [ CAS Unavailable ]
YieldReaction ConditionsOperation 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.
  • 11
  • [ 526-95-4 ]
  • benzyl(dimethyl)[3-(tetradecanoylamino)propyl]ammonium chloride [ No CAS ]
  • myramistin D-gluconate [ No CAS ]
YieldReaction ConditionsOperation 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.
  • 12
  • [ 15809-19-5 ]
  • [ CAS Unavailable ]
  • [ 2704534-36-9 ]
YieldReaction ConditionsOperation 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.
  • 13
  • [ 56-41-7 ]
  • [ 15809-19-5 ]
  • [ 2704606-05-1 ]
YieldReaction ConditionsOperation 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.
  • 14
  • [ 61-90-5 ]
  • [ 15809-19-5 ]
  • [ 2704606-09-5 ]
YieldReaction ConditionsOperation 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.
  • 15
  • [ 15809-19-5 ]
  • [ 73-22-3 ]
  • [ 2704606-11-9 ]
YieldReaction ConditionsOperation 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.
  • 16
  • [ 56-84-8 ]
  • [ 15809-19-5 ]
  • [ 2704606-13-1 ]
YieldReaction ConditionsOperation 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.
  • 17
  • [ 59-67-6 ]
  • [ 15809-19-5 ]
  • [ 2704606-14-2 ]
YieldReaction ConditionsOperation 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.
  • 18
  • [ 15809-19-5 ]
  • [ 81-07-2 ]
  • [ 2704606-15-3 ]
YieldReaction ConditionsOperation 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.
  • 19
  • [ 15809-19-5 ]
  • [ CAS Unavailable ]
  • [ 2704605-85-4 ]
YieldReaction ConditionsOperation 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.
  • 20
  • [ 15809-19-5 ]
  • [ CAS Unavailable ]
  • [ 2704605-97-8 ]
YieldReaction ConditionsOperation 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.
  • 21
  • [ 15809-19-5 ]
  • [ CAS Unavailable ]
  • [ 2704605-99-0 ]
YieldReaction ConditionsOperation 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.
  • 22
  • [ 15809-19-5 ]
  • [ 65-85-0 ]
  • [ 2704605-79-6 ]
YieldReaction ConditionsOperation 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).
  • 23
  • [ 15809-19-5 ]
  • [ CAS Unavailable ]
  • [ 2704605-78-5 ]
YieldReaction ConditionsOperation 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).
  • 24
  • [ 15809-19-5 ]
  • [ 544-63-8 ]
  • [ 2704534-30-3 ]
YieldReaction ConditionsOperation 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).
  • 25
  • [ 26811-96-1 ]
  • [ 15809-19-5 ]
  • [ 2704605-81-0 ]
YieldReaction ConditionsOperation 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).
  • 26
  • [ CAS Unavailable ]
  • [ 15809-19-5 ]
  • [ 2704605-80-9 ]
YieldReaction ConditionsOperation 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).
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