N-Lauroyl-L-glutamic acid

The molar ratio of raw material methyl laurate and sodium glutamate of 1.8: 0.7 was chosen to mix potassium oxide in a molar ratio of 2: 1And magnesium oxide is a metal oxide catalyst, and the catalyst is added in an amount of 0.05 wtpercent of the total amount of the reactants.The synthesis was prepared according to the one-step synthesis method in Example 1, in which the reaction temperature of the primary mixer was generally controlled at20 to 30 degrees, in particular, a mixer inlet temperature control at 25 degrees, a mixer outlet temperature control at25 degrees; pH maintained at 10. The reaction temperature of the secondary mixer is generally controlled between 30 and 40 degrees. Specifically, the secondary mixingThe feed inlet temperature control 35 degrees, two mixer outlet temperature control at 35 degrees; pH maintained at 13.After the reaction was completed, 0.069percent methanol was separated to obtain lauroyl glutamic acid having an active content of 88.67percentSodium, purity up to 98percent.General procedure: Commercially available ionized liquid tetrabutylphosphonium glycinate (Gly-TBP, manufactured by Katayama Pharmaceutical Co., Ltd., colorless transparent liquid, moisture content: 0.11 mass percent) was used as the component (A).In a high purity argon atmosphere, Lau-OMe was added to 1 kg of the above Gly-TBP so that the amount of methyl laurate (Lau-OMe, Wako Pure Chemical Industries, Ltd.) was 500 mmol (Gly-TBP: Lau-OMe molar ratio = 6: 1). After thorough stirring of the obtained solution, it was confirmed that the whole solution became homogeneous, and then the reaction was started by heating to 60 ° C. while stirring in a water bath. Each time-lapse sample was analyzed by HPLC to confirm formation of N-acylamino acid (N-lauroylglycine). After 86 hours, the yield of N-acylamino acid (N-lauroylglycine) was about 82percent20.44 g of lauric acid (content of 98%) and 20.84 g of N, N'-dicyclohexylcarbodiimide (DCC) (content: 99%) were added to a ball mill and ground for 30 min. Add 14.86 g of glutamic acid (99%) and 8.42 g of sodium bicarbonate. After continuing to grind for 45 min, a white solid product was obtained which was the target collector product. After analysis and testing, The collector product 2-lauroamide glutaric acid content is 52.12%, The yield of 2-lauroyl glutaric acid based on lauric acid was 96.28%.The result of analysis of the crystals in the same manner as in indicated that the yield of the Preferred examples of which include:...N-lauroyl aspartic acidN-palmitoyl aspartic acidN-octanoyl aspartic acidN-acetyl glutamic acidN-lauroyl glutamic acidN-palmitoyl glutamic acidN-octanoyl glutamic acidN-acetyl arginine...Examples of which include: ... N-octanoyl aspartic acid N-acetyl glutamic acid N-lauroyl glutamic acid N-palmitoyl glutamic acid ...Preferred examples of which include: ... N-octanoyl aspartic acid N-acetyl glutamic acid N-lauroyl glutamic acid N-palmitoyl glutamic acid ...General procedure: Commercially available ionized liquid tetrabutylphosphonium glycinate (Gly-TBP, manufactured by Katayama Pharmaceutical Co., Ltd., colorless transparent liquid, moisture content: 0.11 mass percent) was used as the component (A).In a high purity argon atmosphere, Lau-OMe was added to 1 kg of the above Gly-TBP so that the amount of methyl laurate (Lau-OMe, Wako Pure Chemical Industries, Ltd.) was 500 mmol (Gly-TBP: Lau-OMe molar ratio = 6: 1). After thorough stirring of the obtained solution, it was confirmed that the whole solution became homogeneous, and then the reaction was started by heating to 60 ° C. while stirring in a water bath. Each time-lapse sample was analyzed by HPLC to confirm formation of N-acylamino acid (N-lauroylglycine). After 86 hours, the yield of N-acylamino acid (N-lauroylglycine) was about 82percentThe molar ratio of raw material methyl laurate and sodium glutamate of 1.8: 0.7 was chosen to mix potassium oxide in a molar ratio of 2: 1And magnesium oxide is a metal oxide catalyst, and the catalyst is added in an amount of 0.05 wtpercent of the total amount of the reactants.The synthesis was prepared according to the one-step synthesis method in Example 1, in which the reaction temperature of the primary mixer was generally controlled at20 to 30 degrees, in particular, a mixer inlet temperature control at 25 degrees, a mixer outlet temperature control at25 degrees; pH maintained at 10. The reaction temperature of the secondary mixer is generally controlled between 30 and 40 degrees. Specifically, the secondary mixingThe feed inlet temperature control 35 degrees, two mixer outlet temperature control at 35 degrees; pH maintained at 13.After the reaction was completed, 0.069percent methanol was separated to obtain lauroyl glutamic acid having an active content of 88.67percentSodium, purity up to 98percent.Weigh lauroyl arginine ethyl ester 76.9 g (0.2 ml), Add 30 mL of ethanol, 60 ° C Water bath dissolved; (2) 0. lmol of lauroylglutamic acid by adding , stirring mixed hook, get salt system; will be obtained in the system vacuum distillation, remove the ethanol; ( 4) the resulting product lauroyl arginine ethyl ester lauroyl glutamate salt is yellow liquid, Freezing point 14 ° C.To a 1000 mL three-necked flask equipped with a thermometer and stirred, 329.5 g (1 mol) of lauroylglutamic acid was added, Anhydrous ethanol 659g, Heating up to 50 ~ 60 deg C to dissolved completely , A phase transfer catalyst PEG-400 was added, 40 g of a granular sodium hydroxide solid was added, 50 ~ 70 deg C under the reaction of 20 ~ 30min, Cooling -5 ~ 5 deg C, Precipitation of white flaky crystals, Filter, After drying, To give 350 g of sodium lauroyl glutamate, Content of 98percent, Yield 99percent. The filtrate was dehydrated by 4A type molecular sieve, filtered and then subjected to atmospheric distillation, Distillation temperature 80 ~ 90 deg C, To obtain a fraction of anhydrous ethanol, The remaining liquid is polyethylene glycol, Are returned to the initial section for recycling. After the molecular sieve drying is activated by drying, Repeated use.The CnGlu analogues were synthesized in our laboratory via a reaction of glutamic acid with octa-, deca-, dodeca-, tetradeca-, or hexadecanoyl chloride in the presence of triethylamine. C12DMA was purchased from Tokyo Chemical Industry and used without further purification. The acid-type CnGlu (1 equiv) was mixed with C12DMA (3 equiv) in ethanol at room temperature for 48 h under magnetic stirring. Then, the solvent was evaporated. The residue was recrystallized from either acetone or a mixture of hexane/ethyl acetate. After filtration, the residue was dried under reduced pressure. We confirmed the formation of a 1:1 stoichiometric complex of CnGlu-C12DMA on the basis of 1H NMR (JEOL-ECP 500 MHz) and ESI-MS (FT-ICR MS Varian 910-MS) data. These characterization data are shown in Supporting Information, Table S1. In typical experiments, the complex (3 wtpercent) was mixed with a NaOH aqueous solution, and the system was heated up to 80 °C. Then the solution was stirred and finally kept for 4 days at a constant temperature of 25 °C. The sample pH was controlled by changing the NaOH concentration.

Molecular Weight:329.4
XLogP3:4.2
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:15
Exact Mass:329.22022309
Monoisotopic Mass:329.22022309
Topological Polar Surface Area:104
Heavy Atom Count:23
Complexity:357
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes