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Product Details of [ 301-02-0 ]

CAS No. :301-02-0 MDL No. :MFCD00053638
Formula : C18H35NO Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 281.48 Pubchem ID :-
Synonyms :
cis-9-Octadecenamide
Chemical Name :(9Z)-9-Octadecenamide

Calculated chemistry of [ 301-02-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 15
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 91.07
TPSA : 43.09 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.05 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.1
Log Po/w (XLOGP3) : 6.99
Log Po/w (WLOGP) : 5.51
Log Po/w (MLOGP) : 4.16
Log Po/w (SILICOS-IT) : 5.71
Consensus Log Po/w : 5.29

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -5.0
Solubility : 0.00282 mg/ml ; 0.00001 mol/l
Class : Moderately soluble
Log S (Ali) : -7.71
Solubility : 0.00000549 mg/ml ; 0.0000000195 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -5.61
Solubility : 0.000689 mg/ml ; 0.00000245 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.97

Safety of [ 301-02-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H317-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 301-02-0 ]

* 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.

  • Downstream synthetic route of [ 301-02-0 ]

[ 301-02-0 ] Synthesis Path-Downstream   1~88

  • 1
  • [ 870-72-4 ]
  • [ 301-02-0 ]
  • [ 17736-09-3 ]
  • 2
  • [ 301-02-0 ]
  • [ 112-91-4 ]
YieldReaction ConditionsOperation in experiment
95% With phosphorus pentoxide at 150℃; for 8h;
60% With thionyl chloride at 80℃; for 4h;
With Ketene at 420℃; ueber Glasringe;
With phosgene at 120 - 130℃;
With phosgene; toluene at 100 - 150℃;
With phosgene; xylene at 100 - 150℃;

  • 3
  • [ 301-02-0 ]
  • [ 15498-10-9 ]
YieldReaction ConditionsOperation in experiment
With peracetic acid; acetic acid
  • 4
  • [ 301-02-0 ]
  • [ 112-20-9 ]
YieldReaction ConditionsOperation in experiment
With copper-chromite-catalyst; ammonia; Petroleum ether unter Druck;
  • 6
  • [ 112-62-9 ]
  • [ 301-02-0 ]
YieldReaction ConditionsOperation in experiment
With ammonia at 165℃;
With ammonia at 165 - 180℃;
With lithium aluminium tetrahydride; ammonia In tetrahydrofuran
  • 7
  • [ 112-77-6 ]
  • [ 301-02-0 ]
YieldReaction ConditionsOperation in experiment
86% With ammonium hydroxide In tetrahydrofuran at 0 - 20℃;
86% With ammonium hydroxide In tetrahydrofuran at 0 - 20℃; for 3h; 1 Step 1 General procedure: To a solution of oleoyl chloride (1 g) in THE (20 mL) was added ammonia hydroxide (10 eq.) at 0° C. The mixture was stirred at room temperature for 3 hours. Then the mixture was filtered to give the desired oleamide 41 as a white solid (796 mg, 86%).
79% With ammonia In dichloromethane; water at 0℃; for 0.5h; 4.1.29 Oleamide (1) The oleyl chloride solution in dry DCM (2mL) was added slowly to aqueous ammonia solution (28-30%, w/w) (30mL) with vigorous stirring at 0°. The mixture was stirred at 0° for half an hour. EtOAc (150mL) and H2O (30mL) were added to the reaction mixture. The organic layer was separated and washed sequentially with saturated aq NaHCO3 (50mL), H2O (50mL), brine (50mL). The EtOAc layer was dried over Na2SO4 and concentrated to dryness under reduced pressure. The crude was purified by flash chromatography on silica gel eluting with hexane/EtOAc (2:1) to give a white solid (2.35g, 79%). Mp 71-73° [lit.47 mp 72-73°]; 1H NMR (400MHz, CDCl3) δ 5.42 (br s, 2H), 5.32-5.39 (m, 2H), 2.22 (t, J=7.2Hz, 2H), 1.98-2.03 (m, 4H), 1.60-1.67 (m, 2H), 1.26-1.31 (m, 20H), 0.88 (t, J=6.8Hz, 3H); 13C NMR (CDCl3, 100MHz) δ 175.73, 130.26, 130.19, 130.02, 129.91, 36.14, 32.13, 29.99, 29.92, 29.76, 29.55, 29.47, 29.34, 27.45, 27.39, 25.75, 22.91, 14.35; LCMS, C18H35NO, [M+H]: 282.
With ammonia
With ammonium hydroxide at 0℃; for 0.0833333h; Yield given;
With ammonium hydroxide at 0℃; for 0.0833333h;
With ammonia
With ammonium hydroxide
With ammonia In water at 20℃; for 0.5h; 1 Under nitrogen atmosphere, oxalyl chroride (0.45ml, 5.3mmol) is dropped into an absolute methylene chloride solution (8.5ml) of 9(Z)-octadecenoic acid (490mg 1.8mmol) cooling the solution with ice. Then the solution was stirred at room temperature for four hours. After the solvent was distilled out and aqueous ammonia (10ml) was added thereto. The solution was stirred at room temperature for 30 minutes. After water (10ml) was added thereto, extraction was performed with ethyl acetate (15ml x 3) added thereto. An organic layer thus obtained was washed with saturated saline (10ml). Next, the organic layer was dried with anhydrous sodium sulfate and then concentrated under reduced pressure, thereby obtaining a crude product. The crude produce was purified using a silica gel column chromatography (hexan: ethyl acetate = 1 : 2). Thereby, octanamide (350mg, 71%) was obtained.1H-NMR (CDCl3, 300MHz): ? 0.88 (3H, t, J=6.4Hz), 1.24 to 1.33 (20H, m), 1.58 to 1.65 (2H, m), 1.99 to 2.02 (4H, m), 2.22 (2H, t, J=7.5 Hz), 5.32 to 5.36 (2H, m).
With ammonia In dichloromethane at 0 - 10℃; for 4.5 - 6.5h; 1.2 Dichloromethane (600.00 kg, 452.83 L) (+/-2%) is charged to the reactor and the stirrer is started. The contents of the reactor are cooled to 0-5 °C. Ammonia (48.00 kg) (+/-2%) is charged as a liquid over 1.5 to 2.0 hours. To the ammonia solution, the oleoyl chloride solution is added over 1.25 to 1.75 hours at 0-10°C. The volume of the medium is about 580 L. The reaction mixture is stirred out at 0-10°C for 1.75 to 2.25 hours. A sample of the reaction mixture is analysed by HPLC (quench sample into MeOH). If the reaction has not proceeded to completion (limit 0.5% acid chloride as the methyl ester by HPLC), then the reaction mixture is stirred out for a further 0.75 to 1.25 hours and resample. At the end, the reaction is quenched by addition of 5M hydrochloric acid solution (400.0 L) (+/-2%). Ammonium chloride formed will dissolve to give two separable layers. The volume of the medium is about 980 L. The lower dichloromethane layer is separated and retained and the upper aqueous layer is removed and discarded. The dichloromethane layer is washed with 1M sodium carbonate solution (2 x 80 L). The maximum approximate volume is 740 L. The combined carbonate washes are extracted and back-extracted with dichloromethane (106.00 kg, 80.00 L) (+/-2%). The combined dichloromethane layers are washed with water (3 x 100 L) (+/-2%). The maximum approximate volume is 760 L. The dichloromethane solution is distilled to minimum stirred volume at atmospheric pressure and then tetrahydrofuran is charged (426.72 kg, 480.00 L)(+/-2%) while continuing the distillation until a pot temperature of >65°C is obtained; the distillate is <1% dichloromethane by Gas Chromatography. If level of dichloromethane is > 1% distillation is continued with addition of tetrahydrofuran until specification is met. The tetrahydrofuran solution is concentrated to ~10% w/w (~220.0 L), removed from the reactor and stored for use in the subsequent reduction reaction.
With ammonia In dichloromethane at 0 - 5℃; for 1h;
With ammonium hydroxide
With ammonia Cooling with ice; General procedure for the amidation of oleic acid General procedure: A round bottom flask, fitted with watercondenser was charged with 20 mL of thionylchloride and 52 mL of oleic acid was added veryslowly through condenser [Please note that rapidaddition can cause bumping or explosion] withconstant stirring into it. After complete additionof oleic acid, the reaction mixture was allowed to heat at 600C for 15 min with continuous stirring.The progress of the reaction was monitored usingTLC. After completion of the reaction, the reactionmixture was allowed to cool in an ice- bath andthe unreacted acid was confirmed by treatingthe reaction mass with 10% sodium bicarbonatesolution. Thereafter, various amines namelyammonia, ethylene diamine, phenyl hydrazine andm-anisidine (m-anisidine was taken into acetone)respectively were added to this ice-cold solution toobtain corresponding amides of oleic acid in goodto excellent yield. The crystals of the crude productwere separated out as a white solid (oleamide),white solid (N-(2-aminoethyl)-oleamide), yellowishsolid ((Z)-N’-phenyloleohydrazide), and pink solid((Z)-N-(3-methoxyphenyl)oleamide), and werecollected over suction pump and stored in adesiccator Scheme 1

Reference: [1]Lin, Hua; Long, Jonathan Z.; Roche, Alexander M.; Svensson, Katrin J.; Dou, Florence Y.; Chang, Mi Ra; Strutzenberg, Timothy; Ruiz, Claudia; Cameron, Michael D.; Novick, Scott J.; Berdan, Charles A.; Louie, Sharon M.; Nomura, Daniel K.; Spiegelman, Bruce M.; Griffin, Patrick R.; Kamenecka, Theodore M. [Journal of Medicinal Chemistry, 2018, vol. 61, # 7, p. 3224 - 3230]
[2]Current Patent Assignee: STATE UNIVERSITY SYSTEM OF FLORIDA - US2020/317613, 2020, A1 Location in patent: Paragraph 0248
[3]Wu, Hui; Kelley, Charles J.; Pino-Figueroa, Alejandro; Vu, Huyen D.; Maher, Timothy J. [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 17, p. 5188 - 5197]
[4]Roe; Scanlan; Swern [Journal of the American Chemical Society, 1949, vol. 71, p. 2217]
[5]Cravatt, Benjamin F.; Lerner, Richard A.; Boger, Dale L. [Journal of the American Chemical Society, 1996, vol. 118, # 3, p. 580 - 590]
[6]Xu, Ming-Zhe; Lee, Woo Song; Kim, Mi Jeong; Park, Doo-Sang; Yu, Hana; Tian, Guan-Rong; Jeong, Tae-Sook; Park, Ho-Yong [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 16, p. 4277 - 4280]
[7]Aschan [Chemische Berichte, 1898, vol. 31, p. 2346] De Bank, Paul A.; Kendall, David A.; Alexander, Stephen P.H. [Biochemical Pharmacology, 2005, vol. 69, # 8, p. 1187 - 1193]
[8]Lees, George; Edwards, Michelle D.; Hassoni, Abdul A.; Ganellin, C. Robin; Galanakis, Dimitrious [British Journal of Pharmacology, 1998, vol. 124, # 5, p. 873 - 882]
[9]Current Patent Assignee: JAPAN SCIENCE AND TECHNOLOGY AGENCY - EP1582219, 2005, A1 Location in patent: Page/Page column 8
[10]Current Patent Assignee: SANTEN PHARMACEUTICAL CO LTD - EP1746084, 2007, A1 Location in patent: Page/Page column 4; 9
[11]Location in patent: experimental part Cheng, Ming-Ching; Ker, Yaw-Bee; Yu, Tung-Hsi; Lin, L.I.-Yun; Peng, Robert Y.; Peng, Chiung-Huei [Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 3, p. 1502 - 1508]
[12]Location in patent: experimental part Divito, Erin B.; Davic, Andrew P.; Johnson, Mitchell E.; Cascio, Michael [Analytical Chemistry, 2012, vol. 84, # 5, p. 2388 - 2394]
[13]Gupta, Gaurav R.; Joshi, Narendra S.; Phalak, Raju P.; Waghulde, Govinda P. [Oriental Journal of Chemistry, 2021, vol. 37, # 5, p. 1109 - 1116]
  • 12
  • [ 112-80-1 ]
  • [ 301-02-0 ]
YieldReaction ConditionsOperation in experiment
98.6% With ammonia; zircornium(IV) n-propoxide at 165℃; for 9h; 16 General procedure: According to the embodiment of the present invention described above, stearic acid amide, which is a kind of carboxylic acid amide compound, was prepared in Example 1 as follows. First, the carboxylic acid injector 250 injects 1000 g of stearic acid into the heater 100, and the heater 100 heats 1000 g of stearic acid to 120 ° C. Subsequently, when stearic acid is injected into the first reaction tank 210, the first catalyst injector 261 injects 10 g of tetraisopropyl titanium, which is a metal catalyst, into the first reaction tank 210, Was heated by the heater attached to the first reaction tank 210. When 150 g of stearic acid was charged into the first reaction tank 210, the first ammonia injector 281 started to feed the ammonia gas through the ammonia pipe 283 at a rate of 100 L / hr. When 500 g of stearic acid was charged into the first reaction tank 210, the introduction of stearic acid into the first reaction tank 210 was stopped. The propeller in the first reaction tank 210 was mixed with stearic acid and ammonia while maintaining the reaction temperature at 165 ° C in the first reaction tank 210.Next, when the supply of the stearic acid to the first reaction tank 210 is stopped, the 500 g of stearic acid remaining in the heater 100 through the valve is changed to be supplied to the second reaction tank 220. When stearic acid is injected into the second reaction tank 220, the second catalyst injector 262 injects 10 g of tetraisopropyl titanium as a metal catalyst into the second reaction tank 220 and starts heating the second reaction tank 220 . When 150 g of stearic acid was charged into the second reaction tank 220, the second ammonia feeder 282 started to feed the ammonia gas through the ammonia pipe 283 at a rate of 100 L / hr. When all 500 g of stearic acid was fed to the second reaction tank, the addition of stearic acid to the second reaction tank was stopped. The propeller in the second reaction tank 220 was mixed with stearic acid and ammonia while maintaining the reaction temperature of 165 ° C in the second reaction tank 220.In Examples 2 to 10, other carboxylic acid amide compounds were prepared in the same manner as in Example 1, except that stearic acid was used instead of stearic acid and other carboxylic acids as shown in the following Table 1 as "acid".
95% With Candida antarctica lipase B; ammonium carbamate In various solvent(s) at 35℃; for 96h;
94% With Candida antarctica lipase B; ammonium carbamate In various solvent(s) at 35℃; for 72h;
90.6% With urea at 160℃; for 2h; 2 In a 100 mL three-necked flask, 5.68 g (0.02 mol) of oleic acid, 2.4 g (0.04 mol) of urea was added, 0. 17g Solid acid catalyst, Mechanical stirring, heating up to 160 ° C, reaction 2h, cooling to about 100 ° C, adding 10% Potassium hydroxide methanol solution and 10mL water, adjust the pH value of the solution 8 ~ 9, hot filter, remove the solid acid catalyst, the filterThe solution was transferred to a 250 mL three-necked flask, 20 mL of absolute ethanol and 1 g of activated carbon were added, heated to reflux for 40 min, filtered while hot,The activated carbon was removed and the filtrate was transferred to a 250 ml beaker, cooled below 0 ° C and filtered to give the crude product. The crude product was recrystallized from acetone to give a white powder as a solid, 50 ° (vacuum drying, weighing 5.18, product yield 90.6%, melting point: 73.4 °C -(75.6 °C).The purity of the oleic acid amide product was 98.6% by HPLC. The acid value of oleic acid amide was 0.3 mgK0H / g and the iodine value was 73.88 g / 100 g according to the national standard GB1668-81 and GB1676-81.
55% With urea at 20 - 195℃; for 0.5h; 4 Oleic acid (25 g, 74% purity) was charged into a 250 ml round bottom flask and then solid urea beads (22 g) were charged into the same flask together with tetra-n-butyl titanate (0.25 g). The mixture was stirred for a minute with a magnetic stirrer in the 900 W microwave oven cavity. The heating program raised the temperature from ambient to 190° C. in 5 minutes and the temperature was maintained at 190° C. for an additional 25 minutes. During the heating process, urea will melt at temperature above 135° C. and begin to decompose at 150° C. liberating NH3 and CO2. The acid value of the reaction product was determined to be about 10 and the conversion percentage of oleic acid to reaction product based on acid value is about 95%.
54% With urea at 20 - 195℃; for 0.5h; 1; 2; 3 Oleic acid (25 g, 74% purity) was charged into a 250 ml round bottom flask and then solid urea beads (22 g) were charged into the same flask together with tetra-n-butyl titanate (0.25 g). The mixture was stirred for a minute with a magnetic stirrer in the 900 W microwave oven cavity. The heating program raised the temperature from ambient to 190° C. in 5 minutes and the temperature was maintained at 190° C. for an additional 25 minutes. During the heating process, urea will melt at temperature above 135° C. and begin to decompose at 150° C. liberating NH3 and CO2. The acid value of the reaction product was determined to be about 10 and the conversion percentage of oleic acid to reaction product based on acid value is about 95%.
52% With urea at 20 - 195℃; for 0.5h; 5 Oleic acid (25 g, 74% purity) was charged into a 250 ml round bottom flask and then solid urea beads (22 g) were charged into the same flask together with tetra-n-butyl titanate (0.25 g). The mixture was stirred for a minute with a magnetic stirrer in the 900 W microwave oven cavity. The heating program raised the temperature from ambient to 190° C. in 5 minutes and the temperature was maintained at 190° C. for an additional 25 minutes. During the heating process, urea will melt at temperature above 135° C. and begin to decompose at 150° C. liberating NH3 and CO2. The acid value of the reaction product was determined to be about 10 and the conversion percentage of oleic acid to reaction product based on acid value is about 95%.
40% Stage #1: cis-Octadecenoic acid With oxalyl dichloride In dichloromethane at 0 - 25℃; for 4h; Stage #2: With ammonium hydroxide In water at 0℃; Synthesis of Oleamide (Ole) Synthesis of Oleamide (Ole) (0075) (0076) A solution of oleic acid (447 mg, 1.58 mmol) in dichloromethane in a 10 mL round bottomed flask was cooled to 0 °C before oxalyl chloride was added dropwise (0.4 mL, 4.74 mmol). The reaction was allowed to heat to 25 °C and left to stir for 4 h. The reaction mixture was concentrated under reduced pressure and again cooled to 0 °C. The concentrate was treated with saturated aq NH4OH (5 mL) for 5 min. The mixture was partitioned between ethyl acetate (10 mL) and water (10 mL), before drying the organic layer over magnesium sulfate. The organic leyer was then concentrated under reduced pressure to yield the crude product. Purification by flash column chromatography (SiO2, 3:2 pentane/ethyl acetate, increasing to 100% ethyl acetate) gave the title compound oleamide (302 mg, 46%) as a white solid. (0077) Rf = 0.22 (Pentane/EtOAc, 3/1); IR (film) υmax 1675, 1467 cm-1 ; 1H NMR (400 MHz, CDCl3) δ 5.35 (m, 4H), 2.23 (t, J = 7.6 Hz, 2H), 2.01 (q, J = 6.1 Hz, 4H), 1.64 (m, 2H), 1.28 (m, 20H), 0.88 (t, J = 6.7 Hz, 3H); 13C NMR (101 MHz, CDCl3) δ 206.80, 130.00, 129.70, 35.90, 31.90, 30.90, 29.70, 29.60, 29.50, 29.30, 29.20, 29.10, 27.20, 27.10, 25.50, 22.70, 14.10; HRMS: (ESI-TOF) calculated for C18H35NO [M - H+] 282.2797, found 294.2803.
35% With ammonium hydroxide; ethanol at 160℃; for 6h; Autoclave; Green chemistry;
10% Stage #1: cis-Octadecenoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: With ammonia In dichloromethane for 12h; (21) General Procedure for Amide Coupling General procedure: To a stirred solution of the fatty acid (1.0 mmol, 1.0 equiv.) inCH2Cl2 (5 mL) was added CDI (0.178 g, 1.1 mmol, 1.1 equiv.).After 30 min at room temperature, the amine (1.1 mmol, 1.1equiv.) was added. After 12 h, CH2Cl2 (25 mL) was added, followedby saturated aqueous NH4Cl. The mixture was acidified topH 2 by addition of HCl, the organic phase was separated, andthe aqueous layer was further extracted with CH2Cl2 (3 × 10mL). The organic phases were combined, dried over Na2SO4, filtered,and concentrated in vacuo, to give the amide.
(i) SOCl2, (ii) NH3, benzene; Multistep reaction;
Multi-step reaction with 2 steps 1: phosphorus trichloride 2: ammonia
Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane / Inert atmosphere 2: ammonium hydroxide
Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane / 4 h / 0 - 20 °C 2: ammonia / dichloromethane; water / 0.5 h / 0 °C
With ammonia In 5,5-dimethyl-1,3-cyclohexadiene Reflux; 6 A solution of 100 g oleic acid and 75 mL of xylenes is heated to reflux with stirring, and NH3 gas is bubbled through the solution for 25-30 hrs. The xylenes are then removed by heating the solution in vacuo to give the crude oleamide product. The oleamides are recrystallized in hot hexanes, followed by cooling of the mixture to 0° C. Oleamide crystals are collected in a Buchner funnel and washed twice with cold hexanes to provide the purified oleamide product.
Multi-step reaction with 2 steps 1: thionyl chloride / 0.25 h / 60 °C 2: ammonia / Cooling with ice

Reference: [1]Current Patent Assignee: Lee, Chang Ho - KR101678461, 2016, B1 Location in patent: Paragraph 0059-0062; 0076
[2]Litjens, Mike J. J.; Straathof, Adrie J. J.; Jongejan, Jaap A.; Heijnen, Joseph J. [Chemical Communications, 1999, # 13, p. 1255 - 1256]
[3]Litjens, Mike J. J.; Straathof, Adrie J. J.; Jongejan, Jaap A.; Heijnen, Joseph J. [Tetrahedron, 1999, vol. 55, # 42, p. 12411 - 12418]
[4]Current Patent Assignee: NANTONG UNIVERSITY - CN104193641, 2016, B Location in patent: Paragraph 0025; 0026
[5]Current Patent Assignee: MPOB - MALAYSIAN PALM OIL BOARD - US2005/283011, 2005, A1 Location in patent: Page/Page column 3
[6]Current Patent Assignee: MPOB - MALAYSIAN PALM OIL BOARD - US2005/283011, 2005, A1 Location in patent: Page/Page column 3
[7]Current Patent Assignee: MPOB - MALAYSIAN PALM OIL BOARD - US2005/283011, 2005, A1 Location in patent: Page/Page column 3
[8]Current Patent Assignee: UNIVERSITY OF DUBLIN; DUBLIN CITY UNIVERSITY; NATIONAL UNIVERSITY OF IRELAND - EP3095444, 2016, A1 Location in patent: Paragraph 0075-0077
[9]Dalu, Francesca; Scorciapino, Mariano A.; Cara, Claudio; Luridiana, Alberto; Musinu, Anna; Casu, Mariano; Secci, Francesco; Cannas, Carla [Green Chemistry, 2018, vol. 20, # 2, p. 375 - 381]
[10]Johansson, Silje J. R.; Johannessen, Tonje; Ellefsen, Christiane F.; Ristun, Mali S.; Antonsen, Simen; Hansen, Trond V.; Stenstrom, Yngve; Nolsoe, Jens M. J. [Synlett, 2019, vol. 30, # 2, p. 213 - 217]
[11]Butenandt,A. et al. [Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1963, vol. 333, p. 114 - 126]
[12]Aschan [Chemische Berichte, 1898, vol. 31, p. 2346]
[13]Divito, Erin B.; Davic, Andrew P.; Johnson, Mitchell E.; Cascio, Michael [Analytical Chemistry, 2012, vol. 84, # 5, p. 2388 - 2394]
[14]Wu, Hui; Kelley, Charles J.; Pino-Figueroa, Alejandro; Vu, Huyen D.; Maher, Timothy J. [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 17, p. 5188 - 5197]
[15]Current Patent Assignee: CALUMET SPECIALTY PRODUCTS PARTNERS LP - US9145535, 2015, B2 Location in patent: Page/Page column 26
[16]Gupta, Gaurav R.; Joshi, Narendra S.; Phalak, Raju P.; Waghulde, Govinda P. [Oriental Journal of Chemistry, 2021, vol. 37, # 5, p. 1109 - 1116]
  • 13
  • [ 3999-01-7 ]
  • [ 301-02-0 ]
YieldReaction ConditionsOperation in experiment
95% With ammonia In dichloromethane for 1h; Ambient temperature;
  • 14
  • [ 77165-66-3 ]
  • [ 301-02-0 ]
YieldReaction ConditionsOperation in experiment
84% With zinc(II) tetrahydroborate In 1,2-dimethoxyethane at 0 - 5℃; for 1.5h;
  • 15
  • [ 112-80-1 ]
  • [ 301-02-0 ]
  • [ 112-62-9 ]
  • [ 638-58-4 ]
  • [ 3843-51-4 ]
YieldReaction ConditionsOperation in experiment
1 % Chromat. With Bacillus megaterium NRRL B-3437; ammonium chloride In water at 28℃; for 96h;
  • 16
  • [ 75-11-6 ]
  • [ 301-02-0 ]
  • [ 10436-16-5 ]
YieldReaction ConditionsOperation in experiment
35% With iodine; copper In toluene for 48h; Heating;
YieldReaction ConditionsOperation in experiment
Ozonisierung in CHCl3;
Rk. mit N-Brom-succinimid, KBr, CCl4, Substitution u. Addition;
der alkal. Hydrolyse (Einfl. d. Konfig.);
With ethylenediaminetetraacetic acid; FAAH from solubilized rat liver crude particulate fraction In ethanol at 20℃; hydrolysis;

YieldReaction ConditionsOperation in experiment
unter verschiedenen Bedingungen;
YieldReaction ConditionsOperation in experiment
With ethanol; ammonia
YieldReaction ConditionsOperation in experiment
With ethanol; ammonia
YieldReaction ConditionsOperation in experiment
With water; zinc(II) oxide at 240℃;
YieldReaction ConditionsOperation in experiment
With ammonia at 110℃;
YieldReaction ConditionsOperation in experiment
at 20 - 25℃;
  • 36
  • [ 301-02-0 ]
  • [ 605-65-2 ]
  • N-(5-(dimethylamino)naphth-1-yl)sulfonyloleamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
18% With sodium hydride In tetrahydrofuran at 20℃; for 3h;
  • 37
  • [ 112-80-1 ]
  • [ 301-02-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalyl chloride 2: ammonia
Multi-step reaction with 2 steps 1: (COCl)2 / CH2Cl2 / 4 h / 20 °C 2: aq. NH4 / 0.08 h / 0 °C
  • 38
  • [ 112-80-1 ]
  • [ 301-02-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: (COCl)2 / CH2Cl2 / 4 h / 25 °C 2: aq, NH4OH / 0.08 h / 0 °C
  • 39
  • [ 60-33-3 ]
  • [ 301-02-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: (COCl)2, DMF / benzene / 3 h / Ambient temperature 2: 95 percent / NH3(gas) / CH2Cl2 / 1 h / Ambient temperature 3: 95 percent / NH3(gas) / CH2Cl2 / 1 h / Ambient temperature
  • 40
  • [ 7459-33-8 ]
  • [ 301-02-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 95 percent / NH3(gas) / CH2Cl2 / 1 h / Ambient temperature 2: 95 percent / NH3(gas) / CH2Cl2 / 1 h / Ambient temperature
YieldReaction ConditionsOperation in experiment
With hydrogen In tetrahydrofuran at 80℃; for 4.5h; 2 Oleic acid amide (13.49 g), diethanolamine (4.51 g) and THF solvent (20 mL) were added to a nitrogen purged reactor by syringe. The reactor was stirred under ca. 200 psi (1380 kPa) of syngas to saturate the solution. After venting, an aliquot (10.4 g) of a pre- made catalyst solution of [Rh (CO) 2 (acac) ] (5351 ppm by weight Rh) and tris (2, 4-di-t- butylphenyl) phosphite ligand (5.00 moles of ligand/mole of Rh) in THF was added to the reactor. The reactor was sealed and pressurized with syngas and heated to 80° C. The pressure was increased to 600 psi (4140 kPa) with additional syngas, and then fed on demand at this pressure throughout the reaction. After 4.5 hours, the reactor was cooled, vented and the reactor contents discharged. The amber solution was extracted with cyclohexane, then toluene, and the supernatent discarded. Acetonitrile was added to the lower brown layer, and stirred briefly. When agitation was ceased, a viscous, honey-colored lower layer was isolated by decantation (16.7 g). H-1 and C-13 NMR spectroscopy showed that the product was the desired with some excess diethanolamine. Mass spectrometry (CI with isobutane) shows a (M+H) + peak at 489 and a (M+H+Isobutene) + peak at 545 confirming the molecular weight.
  • 42
  • [ 301-02-0 ]
  • 8-[(2S*3R*)-3-octyloxirane-2-yl]octanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 3h; 2 Cooling with ice, m-chloro perbenzoic acid (49mg, 0.23mmol) was added to methylene chloride solution (3ml) of oleamide (53mg, 0.19mmol) obtained in Example 1, thereby preparing a solution. The solution was stirred at room temperature for three hours. Cooling with ice, saturated sodium thiosulfate aqueous solution (3ml) was also added thereto, and then extraction was performed with ethyl acetate (5ml x 3). An organic layer thus obtained was washed with saturated saline (10ml). Next, the organic layer was dried with anhydrous sodium sulfate sulfate and then concentrated under reduced pressure, thereby obtaining a crude product. The crude product was purified using silica gel column chromatography (ethyl acetate). In this way, oxirane-containing amide (MI-18): 8-[(2S*3R*)-3-octyloxirane-2-yl] octanamide (54 mg, 96%) was obtained. This oxirane-containing amide was one of the compounds contained in the general formula (1).
  • 43
  • EtOAc-hexanes [ No CAS ]
  • [ 79-37-8 ]
  • aqueous NH4OH [ No CAS ]
  • [ 112-80-1 ]
  • [ 301-02-0 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane 1 1. 1. Cis-9,10-octadecenoamide (1:): A solution of oleic acid (1.0 g, 3.55 mmol, 1.0 equiv.) in CH2Cl2 (8.9 mL, 0.4 M) at 0° C. was treated dropwise with oxalyl chloride (5.32 mL, 2.0 M solution in CH2Cl2, 10.64 mmol, 3.0 equiv.). The reaction mixture was stirred at 25° C. for 4 h, concentrated under reduced pressure, cooled to 0° C., and treated with saturated aqueous NH4OH (2.0 mL). The reaction mixture was then partitioned between ethyl acetate (EtOAc) (100 mL) and H2O (100 mL), and the organic layer was dried (Na2SO4) and concentrated under reduced pressure. Chromatography (SiO2, 5 cm*15 cm, 40-100% EtOAc-hexanes gradient elution) afforded 1 as a white solid (0.810 g, 0.996 g theoretical, 81.3%): 1H NMR (CDCl3, 250 MHz) δ 6.06 (bs, 1H, NH2C(O)), 5.58 (bs, 1H, NH2C(O)), 5.32 (m, 2H, CH=CH), 2.16 (t, 2H, J 7.5 Hz, CH2C(O)NH2), 2.02 (m, 4H, CH2CH=CHCH2), 1.61 (m, 2H, CH2CH2C(O)NH2), 1.29 (b s, 14H, alkyl protons), 0.87 (t, 3H, CH3); FABHRMS (NBA/NaI m/e 282.2804 (C18H35NO+H+requires 282.2797).
  • 44
  • EtOAc-hexanes [ No CAS ]
  • [ 301-02-0 ]
  • 9-T-butyldiphenylsilyloxy-nonanal [ No CAS ]
YieldReaction ConditionsOperation in experiment
94.9% With diisobutylaluminium hydride In methanol; toluene 21 21. 21. 9-T-butyldiphenylsilyloxy-nonanal (Intermediate for Compound 100:) A solution of 1 (1.25 g, 2.93 mmol, 1.0 equiv) in toluene (9.80 mL, 3.0 M) at -78° C. was treated dropwise with DIBAL-H (4.40 mL, 1.0 M solution in hexanes, 4.40 mmol, 1.5 equiv). The reaction mixture was stirred at -78° C. for 30 min. The reaction mixture was then treated dropwise with MeOH (2 mL) and partitioned between EtOAc (100 mL) and H2O (100 mL). The organic layer was washed with 10% aqueous HCl (100 mL), dried (Na2SO4), and concentrated under reduced pressure. Chromatography (SiO2, 5 cm*15 cm, 0-5% EtOAc-hexanes gradient elution) afforded 3 as a colorless oil (1.1 g, 94.9%): 1H NMR (CDCl3, 250 MHz) δ 9.76 (t, 1H, J=1.8 Hz, HC(O)R), 7.67 (m, 4H, ArH), 7.40 (m, 6H, ArH), 3.65 (t, 2H, J=6.4 Hz, CH2OTBDPS), 2.41 (t of d, 2H J=1.8 and 7.3 Hz, CH2C(O)H), 1.58 (m, 4H, CH2CH2OTBDPS and CH2CH2C(O)H), 1.29 (b s, 8H, alkyl protons), 1.05 (s, 9H, (CH3)3C); FABHRMS (NBA/CsI) m/e 529.1560 (C25H3602Si+Cs+requires 529.1539).
  • 45
  • EtOAc-hexanes [ No CAS ]
  • [ 79-37-8 ]
  • aqueous NH4 OH [ No CAS ]
  • [ 112-80-1 ]
  • [ 301-02-0 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane Synthetic Methods Cis-9,10-octadecenoamide (1). A solution of oleic acid (1.0 g, 3.55 mmol, 1.0 equiv.) in CH2 Cl2 (8.9 mL, 0.4M) at 0° C. was treated dropwise with oxalyl chloride (5.32 mL, 2.0M solution in CH2 Cl2, 10.64 mmol, 3.0 equiv.). The reaction mixture was stirred at 25° C. for 4 h, concentrated under reduced pressure, cooled to 0° C., and treated with saturated aqueous NH4 OH (2.0 mL). The reaction mixture was then partitioned between ethyl acetate (EtOAc) (100 mL) and H2 O (100 mL), and the organic layer was dried (Na2 SO4) and concentrated under reduced pressure. Chromatography (SiO2, 5 cm*15 cm, 40-100% EtOAc-hexanes gradient elution) afforded 1 as a white solid (0.810 g, 0.996 g theoretical, 81.3%): 1 H NMR (CDCl3, 250 MHz) δ6.06 (bs, 1H, NH2 C(O)), 5.58 (bs, 1H, NH2 C(O)), 5.32 (m, 2H, CH=CH), 2.16 (t, 2H, J=7.5 Hz, CH2 C(O)NH2), 2.02 (m, 4H, CH2 CH=CHCH2), 1.61 (m, 2H, CH2 CH2 C(O)NH2), 1.29 (b s, 14H, alkyl protons), 0.87 (t, 3H, CH3); FABHRMS (NBA/NaI m/e 282.2804 (C18 H35 NO+H+ requires 282.2797).
  • 46
  • [ 112-77-6 ]
  • [ 301-02-0 ]
  • [ 112-80-1 ]
YieldReaction ConditionsOperation in experiment
With ammonia In dichloromethane at 0 - 20℃; 3 To a 5-litre flange neck flask fitted with overhead stirrer, temperature probe, nitrogen inlet and a 500 cm3 dropping funnel was charged oleic acid (400.0 g, 1.416 mol) and dichloromethane (3.20 L). The resultant solution was heated to reflux (39-41°C) and thionyl chloride (202.4 g, 1.2 eq.) added over 10 minutes between 39-41°C. The reaction mixture was heated at reflux for 3.0 hours, sampling the mixture at hourly intervals (sample quenched into anhydrous methanol, shaken well, and stored at ambient for >1 hour before submitted to analytical development for analysis). The reaction was shown to be 99.9% complete after 3 hours. As the reaction mixture was used in the subsequent amidation reaction without delay, no isomerisation to the trans-isomer was observed. To a 20-litre flange-neck flask fitted with overhead stirrer, nitrogen inlet, condenser (with silica drying tube) and a gas sparging inlet was charged dichloromethane (12.00 Kg, ~9.1 L). The solvent was cooled to 0-10 °C and then ammonia (960 g) was charged as a gas via the sparging inlet over 140 minutes, maintaining the reaction mixture between 0-10°C. The acid chloride solution in dichloromethane was then added to the stirred ammonia solution via transfer line and 500 cm3 dropping funnel over 32 minutes, maintaining the reaction temperature below 20°C. The resultant pink-coloured suspension was allowed to stir at ambient temperature overnight. A sample was taken (sample quenched into methanol). The reaction mixture was shown to be 76.69% oleylamide and 22.53% oleic acid. The reaction mixture was quenched by addition of 5M hydrochloric acid solution (8.00 L) over 15 minutes, maintaining the internal temperature of the reaction mixture below 30°C. The quenched mixture was stirred for 10 minutes, transferred to a 20-litre separatory funnel, and allowed to separate (clean separation with good interface achieved). The lower organic layer was removed and retained. The upper aqueous layer was removed and discarded. The dichloromethane solution was then washed with 1M sodium carbonate solution (2 x 1.60 L). The level of oleic acid was reduced from 24.13% to 13.56% after one wash and to 1.19% after the second wash. The resultant product solution was then washed with water (3 x 1.60 L) (pH of final wash = 8.6) and evaporated to dryness to yield the crude amide as a yellow crystalline solid (284.6 g, 71%). This material was shown to be 97.41% oleylamide and 1.39% oleic acid by HPLC. A 25.0 g portion of the batch was recrystallised from acetonitrile (125 cm3, 5 volumes) to yield 23.8 g purified oleylamide suitable for characterisation as a reference marker. The main characteristics are gathered in Table 2 below
  • 47
  • [ 301-02-0 ]
  • [ 112-90-3 ]
YieldReaction ConditionsOperation in experiment
95% With lithium aluminium tetrahydride In tetrahydrofuran Reflux; 4.1.30 Oleylamine (1i) To a solution of 1 (2.1g, 7.47mmol) in dry THF (10mL) was added 10.5ml (10.46mmol) of 1.0M LAH solution in THF so that gentle reflux was maintained. The reaction mixture was allowed to stir at room temperature overnight. It was then hydrolyzed by cautiously adding dropwise aqueous NaOH (2N, 10mL), extracted with ethyl ether (2×80mL). The combined organic layers was washed with H2O (50ml), brine (50mL), dried over Na2SO4 and evaporated in vacuo to yield a colorless oil (1.9g, 95%). 1H NMR (400MHz, CDCl3) δ 5.33-5.36 (m, 2H), 2.68 (t, J=7.2Hz, 2H), 1.99-2.04 (m, 4H), 1.42-1.45 (m, 2H), 1.20-1.29 (m, 24H), 0.88 (t, J=6.8Hz, 3H); LCMS, C18H37N, [M+H]: 268.
95% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux;
95% With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Reflux; 2 Step 2 General procedure: To a suspension of LiAlH4 (2 eq.) in THE was added oleamide in one portion at 0° C. The mixture was heated to reflux overnight. Then the mixture was quenched with water (3 drops) at 0° C., added with 1 M NaOH solution, stirred at room temperature for 1 hour. The suspension was filtered through celite. The filtrate was diluted with EA, washed with water and brine, dried over anhydrous Na2SO4, filtered and concentrated to give (Z)-octadec-9-en-1-amine 42 (726 mg, 95%) which was used for the next step without further purification
Stage #1: cis-9-octadecenoamide With lithium aluminium tetrahydride In tetrahydrofuran at 50 - 60℃; for 3.5 - 6.75h; Stage #2: With sodium hydroxide; water In tetrahydrofuran at 40℃; for 1 - 2h; 1.3 1.0 M lithium aluminium hydride solution is charged in tetrahydrofuran (160.20 kg, 177.02 L) (+/-1%) to the reactor and the stirrer is started. The reactor contents are heated to 50-60°C. To the lithium aluminium solution the amide solution in tetrahydrofuran is charged over 1.75 to 2.25 hours, maintaining the reaction temperature between 50-60°C. The approximate volume is 397.0 L. The reaction is stirred at 50-60°C for 1.75 to 2.25 hours. The reaction mixture is sampled and analysed by gas chromatography GC (quench sample into excess 32% NaOH solution and remove lower aqueous layer). The limit is 0.5% oleylamide by GC. If the reaction has not proceeded to completion, the medium is stirred-out for a further 0.75 to 1.25 hours and resampled. The reaction mixture is cooled to 15-25°C. Into the larger paired reactor 32% w/w sodium hydroxide solution is charged in water (800.00 Kg) (+/-5%). Approximate volume is 595 L. The reaction mixture is charged to the sodium hydroxide solution via the charge vessel over 1.0 to 2.0 hours, maintaining the temperature of the reactor contents below 40°C. Approximate volume is 995 L. T-butyl methyl ether (148.00 kg, 200.00 L)(+/-2%) is charged to the reactor and stirred for 0.25 to 0.75 hours. The mixture is allowed to separate. Approximate volume is 1 195 L. The lower aqueous layer is separated and retained. The upper organic layer is removed and retained. The aqueous layer is re-extracted with t-butyl methyl ether (74.00 kg, 100.00 L) (+/-2%). Approximate volume is 670 L. The combined organic layers are washed with deionised water (3 x 200 L) (+/-5%). Approximate maximum volume is 520 L. The resultant organic solution is concentrated to give a ~15-20% w/v solution of crude product in t-butyl methyl ether (containing ~15 Kg of oleylamine). Approximate volume is 90 L.

  • 48
  • [ 301-02-0 ]
  • C97H171N17O33 [ No CAS ]
  • C169H303N21O33 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h;
  • 49
  • [ 301-02-0 ]
  • [ 71989-31-6 ]
  • [ 71989-33-8 ]
  • [ 71989-26-9 ]
  • [ 119831-72-0 ]
  • C56H105N9O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70.8% Stage #1: cis-9-octadecenoamide With sodium cyanoborohydride; acetic acid In methanol; N,N-dimethyl-formamide at 80℃; for 2.5h; solid phase reaction; Stage #2: Fmoc-Arg(Pbf)-OH With benzotriazol-1-ol; diisopropyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 2h; solid phase reaction; Stage #3: Fmoc-Pro-OH; Fmoc-Ser(tBu)-OH; Fmoc-Lys(tert-butoxycarbonyl) Further stages;
  • 50
  • [ 301-02-0 ]
  • [ 1323108-64-0 ]
  • [ 629-54-9 ]
  • [ 124-26-5 ]
  • [ 112-69-6 ]
  • [ 124-28-7 ]
  • [ 1323108-61-7 ]
  • [ 14727-68-5 ]
  • 51
  • [ 124-40-3 ]
  • [ 2733-91-7 ]
  • [ 301-02-0 ]
  • [ 1323108-64-0 ]
  • [ 629-54-9 ]
  • [ 124-26-5 ]
  • 52
  • [ 1196-92-5 ]
  • [ 301-02-0 ]
  • [ 58493-49-5 ]
YieldReaction ConditionsOperation in experiment
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 15h;
  • 53
  • [ 301-02-0 ]
  • [ 630-10-4 ]
  • [ 5743-04-4 ]
  • [(CdSe)13(oleylamine)13] [ No CAS ]
YieldReaction ConditionsOperation in experiment
In not given elem. anal.;
  • 54
  • [ 301-02-0 ]
  • [(CdSe)13(n-octylamine)13] [ No CAS ]
  • [(CdSe)13(oleylamine)13] [ No CAS ]
YieldReaction ConditionsOperation in experiment
In toluene Sonication; excess of oleylamine; elem. anal.;
  • 55
  • [ 301-02-0 ]
  • [ 1450603-58-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / Reflux 2: N,N-dimethyl acetamide / 20 °C
  • 56
  • [ 301-02-0 ]
  • [ 1450603-59-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / Reflux 2: N,N-dimethyl acetamide / 20 °C
  • 57
  • [ 301-02-0 ]
  • [ 126-30-7 ]
  • N-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)oleamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2,2-Dimethyl-1,3-propanediol With trichlorophosphate Stage #2: cis-9-octadecenoamide 21 A',-(5,5-Dirnethy-2-oxido-l ,3,2-dioxaphosphinan-2-yl)oearnide (0506) (Compound 122) Compound 122 was prepared from oleic acid, 2,2-dimethylpropane- l ,3- diol, and phosphorus oxychloride. Briefly, 2,2-dimethylpropane- 1 ,3-diol was treated with phosphorus oxychloride to form the corresponding cyclic chlorophosphate that was then reacted with oleic amide to provide Compound 122. [M+H]" calcd for C23H44NO4P: 430.30; found: 430.6. NMR (400V Hz. CD3OD) 5.35 (bs, 2H), 4.40 (d, ,/ 10, 21 1 ;·. 4.01 (dd, ./ 7,2, 3H),
  • 58
  • [ 67-56-1 ]
  • [ 301-02-0 ]
  • [ 201230-82-2 ]
  • C20H39NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
27% With pyridine; [{1,2-(tBu2PCH2)2C6H4}Pd(OTf)](OTf) at 90℃; for 90h; Schlenk technique; Autoclave;
  • 59
  • [ 301-02-0 ]
  • methyl 18-aminooctadecanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: [{1,2-(tBu2PCH2)2C6H4}Pd(OTf)](OTf); pyridine / 90 h / 90 °C / 15001.5 Torr / Schlenk technique; Autoclave 2: trifluoroacetic acid; [bis(acetoxy)iodo]benzene / tetrahydrofuran; water / 23 h / 20 °C / Darkness
  • 60
  • [ 301-02-0 ]
  • [ 72849-40-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: thionyl chloride / 4 h / 80 °C 2: [{1,2-(tBu2PCH2)2C6H4}Pd(OTf)](OTf); pyridine / 90 h / 90 °C / 15001.5 Torr / Schlenk technique; Autoclave 3: hydrogen; potassium hydroxide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / toluene / 40 h / 80 °C / Autoclave; Schlenk technique
  • 61
  • [ 301-02-0 ]
  • C20H37NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride / 4 h / 80 °C 2: [{1,2-(tBu2PCH2)2C6H4}Pd(OTf)](OTf); pyridine / 90 h / 90 °C / 15001.5 Torr / Schlenk technique; Autoclave
  • 62
  • [ 301-02-0 ]
  • [ 100-46-9 ]
  • [ 101762-87-2 ]
YieldReaction ConditionsOperation in experiment
90% With Ce(III) immobilised on an aminated epichlorohydrin-activated agarose matrix at 140℃; for 25h; Green chemistry; General procedure for transamidation of benzamide with benzylamine using CAEA and recovery of CAEA General procedure: CAEA (0.01 g) was added to a mixture of benzamide (1 mmol, 0.121 g) and benzylamine (1.1 mmol, 0.117 g) in a round-bottom flask equipped with a condenser under solvent-free conditions. The reaction mixture was stirred (250 min-1) at 140 °C. The progress of the reaction was monitored by TLC. Following the reaction, the reaction mixture was cooled and the resultant mixture was submitted to silica gel preparative TLC using ethyl acetate/hexane (1/1) as eluent. N-Benzylbenzamide was obtained with a 95 % yield (0.198 g). The spectral data of the compounds are given in Tables 1 and 2. The reaction mixture was centrifuged (1000 min-1,10 min) and washed several times with ethyl acetate and acetone to remove all the organic compounds then the precipitate was dried at ambient temperature.
  • 63
  • [ 301-02-0 ]
  • [ 2386-60-9 ]
  • (Z)-N-(octadec-9-en-1-yl)butane-1-sulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: cis-9-octadecenoamide; perfluoro-1-butanesulfonyl fluoride With dmap; triethylamine In dichloromethane Cooling with ice; Stage #2: With perfluoro-1-butanesulfonyl fluoride In dichloromethane at 20℃; for 12h; General method for the synthesis of compounds 23-26 General procedure: The method of the synthesis of compounds 23-26 wereshown in Scheme 3. Oleylamine (1 mmol), Et3N (0.27 mL,2 mmol) and DMAP (15 mg) in anhydrous CH2Cl2 (12 mL)were poured into a two flask. The solution was cooled in anice bath and magnetically stirred. Sulfonyl chloride wasadded dropwisely. The reaction mixture was stirred for 12 hat room temperature and then washed with 5%sodiumbicarbonate solution, 1M HCl and brine. The organic layerwas dried over anhydrous Na2SO4, filtered, and concentratedunder reduced pressure. The residue was purified by flash chromatography on silica gel to afford compounds23-26.
  • 64
  • [ 301-02-0 ]
  • [ 136738-80-2 ]
  • 3,5-di-O-benzoyl-1,2-O-(1-oleamidobenzylidene)-α-D-ribofuranose [ No CAS ]
  • 1-N-oleanoly-2,3,5-tri-O-benzoyl-β-D-ribofuranosylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 14.8% 2: 19% With 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea; 3-dodecyl-2-iodo-1-(4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-3-ium trifluoromethanesulfonate In dichloromethane at 20℃; for 24h; Molecular sieve; Inert atmosphere;
  • 65
  • [ 301-02-0 ]
  • [ 136738-80-2 ]
  • 1-N-oleanoly-2,3,5-tri-O-benzoyl-β-D-ribofuranosylamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea; 2-iodo-1-(4-(trifluoromethyl)phenyl)-1H-phenanthro[9,10-d]imidazol-3-ium trifluoromethanesulfonate In dichloromethane at 20℃; for 24h; Molecular sieve; Inert atmosphere;
  • 66
  • [ 301-02-0 ]
  • [ 108869-64-3 ]
  • 3,4,6-tri-O-benzyl-1,2-O-[1-oleamidoethylidene]-α-D-glucopyranose [ No CAS ]
  • 1-N-oleanoly-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-gulcopyranosyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 62% 2: 16% With 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea; 3-dodecyl-2-iodo-1-(4-(trifluoromethyl)phenyl)-1H-benzo[d]imidazol-3-ium trifluoromethanesulfonate In dichloromethane at 20℃; for 24h; Molecular sieve; Inert atmosphere;
  • 67
  • [ 301-02-0 ]
  • [ 108869-64-3 ]
  • 1-N-oleanoly-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-gulcopyranosyl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With 1,3-bis(3,5-bis(trifluoro-ethyl)phenyl)thiourea; 2-iodo-1-(4-(trifluoromethyl)phenyl)-1H-phenanthro[9,10-d]imidazol-3-ium trifluoromethanesulfonate In dichloromethane at 20℃; for 24h; Molecular sieve; Inert atmosphere;
  • 68
  • [ 301-02-0 ]
  • N-((Z)-octadec-9-en-1-yl)-1H-imidazole-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C
  • 69
  • [ 301-02-0 ]
  • C22H42N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C
  • 70
  • [ 301-02-0 ]
  • N-(((Z)-octadec-9-en-1-yl)carbamoyl)glycine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 4: lithium hydroxide / water; tetrahydrofuran / 3 h / 20 °C
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 4: lithium hydroxide; water / tetrahydrofuran / 3 h / 20 °C
  • 71
  • [ 301-02-0 ]
  • [ 1606178-86-2 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C
  • 72
  • [ 301-02-0 ]
  • N-(((Z)-octadec-9-en-1-yl)carbamoyl)-L-phenylalanine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Reflux 2: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C 3: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C 4: lithium hydroxide / water; tetrahydrofuran / 3 h / 20 °C
  • 73
  • [ 301-02-0 ]
  • C34H39N4O7PolS [ No CAS ]
  • [ 109425-51-6 ]
  • Nα-Fmoc-Arg(Ng-Pbf)-OH [ No CAS ]
  • C66H110N28O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: C34H39N4O7PolS; Fmoc-His(Trt)-OH With piperidine In N,N-dimethyl-formamide Inert atmosphere; Stage #2: Nα-Fmoc-Arg(Ng-Pbf)-OH With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Stage #3: cis-9-octadecenoamide; Fmoc-His(Trt)-OH; Nα-Fmoc-Arg(Ng-Pbf)-OH Further stages; 3.1.3. Synthesis of Lauryl-(HR)4 Peptide General procedure: The synthesis of fatty acyl derivatives of linear (HR)4 peptides were carried on solid-phase.The peptide was synthesized using Fmoc-Arg(Pbf)-Wang resin (0.3 mmol, 750.0 mg, 0.40 mmol/g).Once, the linear peptide was assembled after coupling Fmoc-His(Trt)-OH (557.74 mg, 0.9 mmol) andFmoc-Arg(Pbf)-OH (583.90 mg, 0.9 mmol) alternatively using HBTU (341.32. mg, 0.9 mmol) andDIPEA (315 L, 1.8 mmol) in DMF for 1 h with Fmoc deprotection in between each coupling cycleusing 20% piperidine in DMF. After the last coupling was completed, the resin was washed with DMF(3 15 mL) followed by N-terminal Fmoc deprotection using 20% piperidine in DMF (2 10 mL,10 min each). Then, lauric acid (180 mg, 0.9 mmol) was coupled to the N-terminal of the linear (HR)4peptide using HBTU (341.32. mg, 0.9 mmol) and DIPEA (315 L, 1.8 mmol) in the DMF. The resin was washed with DCM (3 25 mL) and methanol (3 25 mL) and vacuum dried. Then the resinand the side chain protecting groups were cleaved from the peptidyl resin using cleavage cocktailTFA/thioanisole/EDT/anisole (90:5:3:2, v:v:v:v, 15 mL) for 5 h. The crude peptide was precipitatedby adding cold diethyl ether (100 mL, Et2O) and centrifuged at 4000 rpm for 10 min, followed bydecantation to obtain the solid precipitate. The solid material was further washed with cold ether(2 100 mL) for 2 times. The peptide was resolubilized in a solvent (CH3CN + 0.1% TFA and water+ 0.1% TFA). The crude peptide was purified by using the reverse-phase high performance liquidchromatography (RP-HPLC) equipped with a Waters XBridgeTM BEH130 Prep C18 column OBDTM10 m (19 mm 250 mm). A gradient of 0-100% acetonitrile and water in 0.1% TFA (v/v) witha flow rate at 10.0 mL/min was used for the purification. The peptide powder was obtained afterlyophilization of pure HPLC fraction. Other fatty acid conjugates of (HR)4 were synthesized in asimilar manner
  • 74
  • [ 301-02-0 ]
  • 10-hydroxy octadecanamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With D-glucose; oleate hydratase variant Gln265Ser/Asn438Asp; water; flavin adenine dinucleotide In aq. phosphate buffer at 30℃; Enzymatic reaction; stereoselective reaction;
  • 75
  • [ 301-02-0 ]
  • dimethyl (Z)-2-(1-aminooctadec-9-en-1-ylidene)malonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetraphosphorus decasulfide / tetrahydrofuran / 2 h / 20 °C 2: methanol / 12 h / 0 °C
  • 76
  • [ 301-02-0 ]
  • tert-butyl (Z)-2-(heptadec-8-en-1-yl)-4-methylthiazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetraphosphorus decasulfide / tetrahydrofuran / 2 h / 20 °C 2: methanol / 12 h / 0 °C
  • 77
  • [ 301-02-0 ]
  • C49H77NO4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetraphosphorus decasulfide / tetrahydrofuran / 2 h / 20 °C 2: methanol / 12 h / 0 °C
  • 78
  • [ 301-02-0 ]
  • C43H67N3O7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetraphosphorus decasulfide / tetrahydrofuran / 2 h / 20 °C 2: methanol / 12 h / 0 °C
  • 79
  • [ 301-02-0 ]
  • C34H55NO7S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetraphosphorus decasulfide / tetrahydrofuran / 2 h / 20 °C 2: methanol / 12 h / 0 °C
  • 80
  • [ 301-02-0 ]
  • but-3-yn-1-yl (Z)-2-(heptadec-8-en-1-yl)-4-methylthiazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: tetraphosphorus decasulfide / tetrahydrofuran / 2 h / 20 °C 2: methanol / 12 h / 0 °C
  • 81
  • [ 301-02-0 ]
  • (Z)-octadec-9-enethioamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With tetraphosphorus decasulfide In tetrahydrofuran at 20℃; for 2h;
  • 82
  • [ 301-02-0 ]
  • [ 80040-79-5 ]
  • 1-N-oleanoly-(2-deoxyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With 2-chloro-1-(4-(trifluoromethyl)phenyl)-1H-phenanthro[9,10-d]imidazol-3-ium trifluoromethanesulfonate In toluene at 30℃; for 48h; Molecular sieve; Inert atmosphere;
  • 83
  • [ 301-02-0 ]
  • [ 80040-79-5 ]
  • [ 380450-55-5 ]
  • 1-N-oleanoly-(2-deoxyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 30 %Spectr. 2: 21 %Spectr. With trifluorormethanesulfonic acid In toluene at 30℃; for 48h; Molecular sieve; Inert atmosphere;
1: 30 %Spectr. 2: 21 %Spectr. With boron trifluoride diethyl etherate In toluene at 30℃; for 48h; Molecular sieve; Inert atmosphere;
  • 84
  • [ 301-02-0 ]
  • [ 1621188-32-6 ]
  • 1-N-oleanoyl-(2-deoxyl-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-β-D-glucopyranosyl)-amine [ No CAS ]
  • C45H91NO6Si3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 2-chloro-1-(4-(trifluoromethyl)phenyl)-1H-phenanthro[9,10-d]imidazol-3-ium trifluoromethanesulfonate In toluene at 70℃; for 5h; Molecular sieve; Inert atmosphere; Overall yield = 52 percent; Overall yield = 34.7 mg;
  • 85
  • [ 79-37-8 ]
  • [ 301-02-0 ]
  • C37H68N2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% for 3h; Inert atmosphere; Schlenk technique; Reflux; 3.2. Synthesis of the target compounds 1 and 2 General procedure: (Z)-Hexadec-9-enamide [or oleamide] (1.0 mmol, 1.0 equiv) was placed in a SchlenkKjeldahl reaction flask and the flask was evacuated/Argon re-filled three times.Subsequently, anhydrous dichloromethane (25 mL) was added and the mixture wasstirred at room temperature (RT) for 5 min before dropwise addition of oxalyl chloride(3.0 mmol, 3.0 equiv) followed. The reaction mixture was then stirred at reflux for3.0 hours before cooling to RT and the solvent was removed under reduced pressurein an air-free manner. Subsequently, (Z)-hexadec-9-enamide [or oleamide] (1.0 mmol,1.0 equiv) was rapidly added via regular powder funnel and the flask was again evacuated/Argon re-filled three times before dry toluene (12 mL) was added. The reactionmixture was then stirred at reflux for another 3 h before cooling to RT and concentrationon rotary evaporator. The isolated crude material was purified by flash chromatographyon silica with gradient of ethyl acetate in hexanes as the eluent.
  • 86
  • [ 301-02-0 ]
  • tetracarboxylic-Fe(II)-phthalocyanine [ No CAS ]
  • C108H148FeN12O8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N,N-dichlorohexylcarbodiimide; potassium carbonate; N,N-dimethyl-formamide at 28℃; Inert atmosphere; 2.2. Synthesis of 9-octadecenamide substituted M(II) phthalocyanine complexes General procedure: A mixture of 9-octadecenamide (0.05 mmol), tetracarboxylic-M(II)- phthalocyanine (0.015 mmol), potassium carbonate (0.05 mmol) and N, N-dichlorohexylcarbodiimide (catalytic quantities, in dimethylformamide 40 mL) was stirred under nitrogen atmosphere for 30 h at 28 C. The green color product was obtained. It was washed with warm water after being washed with methanol followed by NaOH, hydrochloric acid, and distilled water. The product was dried in the oven for 45 min at 40-50 ο C (Scheme 1). Yield 60% [36,37]. Anal. For ODAFePc with molecular weight and molecular formula 1799.01 (Experimental): C108H150FeN12O8 calc. (%) C-72.053, H-8.3974, N-9.3364, O-7.1096, Fe; 3.102 found: C-71.932, H-8.301, N-9.301, O-7.001, Fe-3.010%. Anal. For ODANiPc with molecular weight and molecular formula 1799.9178 (Experimental): C108H150NiN12O8 calc. (%) C-72.053, H-8.3974, N-9.3364, O-7.1096, Ni; 3.260 found: C-71.900, H-8.300, N-9.291, O-7.101, Ni-3.200%.
  • 87
  • [ 301-02-0 ]
  • tetracarboxylic-Ni(II)-phthalocyanine [ No CAS ]
  • C108H148N12NiO8 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N,N-dichlorohexylcarbodiimide; potassium carbonate; N,N-dimethyl-formamide at 28℃; Inert atmosphere; 2.2. Synthesis of 9-octadecenamide substituted M(II) phthalocyanine complexes General procedure: A mixture of 9-octadecenamide (0.05 mmol), tetracarboxylic-M(II)- phthalocyanine (0.015 mmol), potassium carbonate (0.05 mmol) and N, N-dichlorohexylcarbodiimide (catalytic quantities, in dimethylformamide 40 mL) was stirred under nitrogen atmosphere for 30 h at 28 C. The green color product was obtained. It was washed with warm water after being washed with methanol followed by NaOH, hydrochloric acid, and distilled water. The product was dried in the oven for 45 min at 40-50 ο C (Scheme 1). Yield 60% [36,37]. Anal. For ODAFePc with molecular weight and molecular formula 1799.01 (Experimental): C108H150FeN12O8 calc. (%) C-72.053, H-8.3974, N-9.3364, O-7.1096, Fe; 3.102 found: C-71.932, H-8.301, N-9.301, O-7.001, Fe-3.010%. Anal. For ODANiPc with molecular weight and molecular formula 1799.9178 (Experimental): C108H150NiN12O8 calc. (%) C-72.053, H-8.3974, N-9.3364, O-7.1096, Ni; 3.260 found: C-71.900, H-8.300, N-9.291, O-7.101, Ni-3.200%.
  • 88
  • [ 112-90-3 ]
  • [ 301-02-0 ]
YieldReaction ConditionsOperation in experiment
97% With C31H29Br2N3Ru; potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol at 70℃; for 24h; regioselective reaction;
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