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Chemical Structure| 544-31-0
Chemical Structure| 544-31-0
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CAS No. :544-31-0 MDL No. :MFCD00020562
Formula : C18H37NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :HXYVTAGFYLMHSO-UHFFFAOYSA-N
M.W :299.49 Pubchem ID :4671
Synonyms :
Palmitoylethanolamide

Safety of [ 544-31-0 ]

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 [ 544-31-0 ]

* 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.

  • Upstream synthesis route of [ 544-31-0 ]
  • Downstream synthetic route of [ 544-31-0 ]

[ 544-31-0 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 141-43-5 ]
  • [ 57-10-3 ]
  • [ 544-31-0 ]
YieldReaction ConditionsOperation in experiment
95.7%
Stage #1: With triethylamine; diisopropyl-carbodiimide In dichloromethane at 20℃; for 4 h;
Stage #2: at 20℃; for 0.5 h; Inert atmosphere
1) under nitrogen at room temperature,Triethylamine (2 ml) was added dropwise to mercaptomethyl resin (2 g,MATRIX-INN), N-hydroxy maleimide (1.1 g, 9.7 mmol) and DMF (40 ml)In the reaction vessel.After stirring at room temperature for 24 hours,Afterwards, stirring was continued for 4 hours at 55 degrees,After cooling to room temperature and filtered to give NHS resin,Using DMF,Distilled water and isopropyl alcohol were washed twice,NHS resin was obtained after vacuum drying.2) palmitic acid (1.465 g, 5.72 mmol) and the above NHS resin (1.50 g),DIC (diisopropylcarbodiimidediisoprpylcarbodiimide, 0.72 g, 5.72 mmol),Triethylamine (2 ml) was suspended in 15 ml of dichloromethane.The mixture was stirred at room temperature for 4 hours.Then filtered (filtrate retained,Appropriate amount of palmitic acid was detected by HPLC,DIC and solvent,For the next batch of reactions),The collected resin using DMF,Water, isopropanol, and dichloromethane were separately washed twice and dried in vacuo to give 1.70 g of dry resin to obtain an immobilized palmitic acid active ester with a loading of -1.0 mmol / g.3) Ethanolamine (93.2 mg, 1.58 mmol) was added to a flask containing active ester (1.75 g) and 50 ml of BAlcohol suspension,For 0.5 hour,Centrifugal removal of solid resin,The resin was washed twice with ethanol (the resin was left after vacuum drying)The combined liquid phase was concentrated under reduced pressure,453 mg of palmitic monoethanolamide (96.6percent yield for ethanolamine) was obtained,Purity> 99.5percent (HPLC).
90%
Stage #1: With 1-[(1-(cyano-​2-​ethoxy-​2-​oxoethylidenaminooxy)​dimethylamino-​morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane; acetonitrile at 20℃; for 0.166667 h; Inert atmosphere
Stage #2: at 20℃; Inert atmosphere
General procedure: These compounds were synthesized according to the procedure described previously with slight modifications (El-Faham and Albericio, 2010) The appropriate acid (0.15 mmol), (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluoro phosphate (COMU, 64.2 mg, 0.15 mmol), and DIPEA (0.05 ml, 0.30 mmol) were dissolved in anhydrous CH2Cl2 (0.5 ml) and CH3CN (2.5 ml) and the resulting orange-red solution was stirred at rt for 10 min under a nitrogen atmosphere. Ethanolamine (3) (0.15 mmol) in CH3CN (0.2 ml) was then injected into the reaction mixture and vigorous stirring at rt was continued until TLC (CH2Cl2/MeOH 98:2) confirmed the completion of the reaction (3–6 h). The reaction mixture was diluted with CH2Cl2 (3 ml) and the resulting mixture was washed with 5percent HCl, saturated NaHCO3 and brine. The organic layer was collected, dried over anhydrous Na2SO4, filtered. The solvent was evaporated under reduced pressure and crude purified by flash chromatography.
72% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 4 h; Inert atmosphere Stepl . Palmitoylethanolamide, 2: EDCl (673 mg, 3.51 mmol), DMAP (44 mg, 0.35 mmol), and ethanolamine (0.141 mL, 2.34 mmol) were added to a solution palmitic acid 1 (300 mg, 1.17 mmol) was stirred in 10 mL of anhydrous ΟΗ2( at 0 °C. The reaction was allowed to stir under argon for 4 hours while warming to room temperature. Upon completion the reaction mixture was diluted with CH2C, washed with water and brine. The organic layer was collected and concentrated. The resulting residue was chromatographed on silica to yield 2 (312 mg, 72percent) as a white solid. XH NMR (500 MHz, CDC13) δ 3.70 - 3.76 (m, 2H), 3.43 (q, J = 5.37 Hz, 2H), 2.17 - 2.24 (m, 2H), 1.64 (quin, J = 7.45 Hz, 2H), 1.52 (d, J = 1.0 Hz, 1H), 1.19 - 1.35 (m, 26H).
Reference: [1] Beilstein Journal of Organic Chemistry, 2009, vol. 5,
[2] Patent: CN107188816, 2017, A, . Location in patent: Paragraph 0048-0052
[3] Chemistry and Physics of Lipids, 2012, vol. 165, # 7, p. 705 - 711
[4] Patent: WO2015/179190, 2015, A1, . Location in patent: Paragraph 0137
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3231 - 3234
[6] Patent: US5925678, 1999, A,
[7] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 4, p. 1520 - 1527
[8] Bioscience, Biotechnology and Biochemistry, 2011, vol. 75, # 4, p. 768 - 770
[9] ChemSusChem, 2015, vol. 8, # 16, p. 2670 - 2680
[10] Green Chemistry, 2018, vol. 20, # 2, p. 375 - 381
  • 2
  • [ 142-91-6 ]
  • [ 141-43-5 ]
  • [ 544-31-0 ]
YieldReaction ConditionsOperation in experiment
89% With sodium ethanolate In methanol; ethanol at 60℃; for 4 h; Inert atmosphere Reference Preparation Example 1
Synthesis of N-(2-hydroxyethyl)palmitamide (Comparative Compound 1)
Isopropyl palmitate (300 g, 1.00 mol) and ethanolamine (82.0 g, 1.34 mol) were heated at 60° C. with stirring under a nitrogen atmosphere, and thereto were added 17.1 g of a sodium ethoxide/ethanol solution (20 wt percent, 50.3 mmol) and methanol (100 ml).
Four hours later, disappearance of the raw material ester was confirmed by TLC analysis, and then methanol (500 ml) was added thereto and the reaction mixture was cooled to room temperature to allow crystallization.
The resultant crystals were filtered off and washed with methanol to give 268 g of the aimed comparative compound 1 (yield: 89percent).
white solid, melting point: 100° C.;
IR (cm-1, ATR method): 3293, 2917, 2849, 1638, 1552, 1056;
1H-NMR (CDCL3, ppm): 0.85 (t, J=7 Hz, 3H), 1.16-1.37 (m, 24H), 1.57-1.66 (m, 2H), 2.19 (t, J=8 Hz, 2H), 3.41 (q, J=5 Hz, 2H), 3.71 (t, J=5 Hz, 2H), 6.05 (bs, 1H).
Reference: [1] Patent: US2016/38443, 2016, A1, . Location in patent: Paragraph 0101; 0102; 0103; 0104; 0105
  • 3
  • [ 141-43-5 ]
  • [ 112-67-4 ]
  • [ 544-31-0 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1991, # 8, p. 2180 - 2188
[2] Tetrahedron Letters, 2002, vol. 43, # 2, p. 277 - 279
[3] Carbohydrate Research, 1976, vol. 46, p. 133 - 137
[4] Molecular Pharmacology, 2003, vol. 63, # 2, p. 429 - 438
[5] European Journal of Pharmacology, 2000, vol. 408, # 2, p. 161 - 168
[6] Patent: US2017/44414, 2017, A1, . Location in patent: Paragraph 0143; 0144
[7] Medicinal Chemistry Research, 2017, vol. 26, # 11, p. 2951 - 2966
  • 4
  • [ 141-43-5 ]
  • [ 112-76-5 ]
  • [ 544-31-0 ]
YieldReaction ConditionsOperation in experiment
95% at 20℃; for 1 h; Cooling with ice General procedure: A solution of fatty acid oleoyl chloride (1.0 mmol) in CH2Cl2 (2 mL) was added dropwise to a solution of ethanolamine (10 mmol) in CH2Cl2 (10 mL) cooled in an ice bath. The reaction mixture was stirred for 1 h at room temperature, then extracted with CHCl3. The organic layer was dried over Na2SO4 and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3 : MeOH=30 : 1) or by recrystallization (AcOEt–hexane) to give N-acylethanolamide.
Reference: [1] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 4, p. 278 - 285
  • 5
  • [ 693-38-9 ]
  • [ 141-43-5 ]
  • [ 544-31-0 ]
Reference: [1] JAOCS, Journal of the American Oil Chemists' Society, 2012, vol. 89, # 7, p. 1305 - 1313
[2] Patent: US2013/303795, 2013, A1, . Location in patent: Paragraph 0069-0074;0076-0082; 0096; 0098
[3] Patent: CN106242988, 2016, A, . Location in patent: Paragraph 0035; 0036
  • 6
  • [ 112-39-0 ]
  • [ 141-43-5 ]
  • [ 544-31-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 17, p. 5255 - 5257
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 2, p. 340 - 347
[3] ChemSusChem, 2015, vol. 8, # 16, p. 2670 - 2680
  • 7
  • [ 628-97-7 ]
  • [ 141-43-5 ]
  • [ 544-31-0 ]
Reference: [1] Beilstein Journal of Organic Chemistry, 2009, vol. 5,
  • 8
  • [ 57-10-3 ]
  • [ 544-31-0 ]
Reference: [1] Tetrahedron Letters, 1980, vol. 21, p. 841 - 844
[2] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 2, p. 340 - 347
[3] Medicinal Chemistry Research, 2017, vol. 26, # 11, p. 2951 - 2966
  • 9
  • [ 141-43-5 ]
  • [ 544-31-0 ]
Reference: [1] Archiv der Pharmazie, 2009, vol. 342, # 1, p. 34 - 40
[2] Patent: WO2006/109321, 2006, A1, . Location in patent: Page/Page column 7
  • 10
  • [ 141-43-5 ]
  • [ 100663-86-3 ]
  • [ 544-31-0 ]
Reference: [1] Chemistry Letters, 1985, p. 701 - 704
  • 11
  • [ 555-44-2 ]
  • [ 141-43-5 ]
  • [ 544-31-0 ]
Reference: [1] Journal of the American Oil Chemists' Society, 1994, vol. 71, # 8, p. 863 - 866
  • 12
  • [ 141-43-5 ]
  • [ 120246-99-3 ]
  • [ 544-31-0 ]
Reference: [1] Patent: WO2006/109321, 2006, A1, . Location in patent: Page/Page column 6-7
[2] Patent: WO2006/109321, 2006, A1, . Location in patent: Page/Page column 8
  • 13
  • [ 141-43-5 ]
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Reference: [1] Patent: WO2006/109321, 2006, A1, . Location in patent: Page/Page column 7-8
  • 14
  • [ 214706-34-0 ]
  • [ 544-31-0 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1992, vol. 40, # 1, p. 122 - 126
  • 15
  • [ 74058-64-3 ]
  • [ 141-43-5 ]
  • [ 544-31-0 ]
Reference: [1] Tetrahedron Letters, 1980, vol. 21, p. 841 - 844
[2] Chemical & Pharmaceutical Bulletin, 1984, vol. 32, # 7, p. 2687 - 2699
[3] Chemical & Pharmaceutical Bulletin, 1984, vol. 32, # 7, p. 2687 - 2699
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