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CAS No. : | 124-07-2 | MDL No. : | MFCD00004429 |
Formula : | C8H16O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | WWZKQHOCKIZLMA-UHFFFAOYSA-N |
M.W : | 144.21 | Pubchem ID : | 379 |
Synonyms : |
Caprylic acid;C8:0 Fatty acid;Octylic acid;Octoic acid;Octic acid;Caprylsaeure
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.88 |
Num. rotatable bonds : | 6 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 42.34 |
TPSA : | 37.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.01 cm/s |
Log Po/w (iLOGP) : | 1.95 |
Log Po/w (XLOGP3) : | 3.05 |
Log Po/w (WLOGP) : | 2.43 |
Log Po/w (MLOGP) : | 1.96 |
Log Po/w (SILICOS-IT) : | 1.77 |
Consensus Log Po/w : | 2.23 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.26 |
Solubility : | 0.793 mg/ml ; 0.0055 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.5 |
Solubility : | 0.0457 mg/ml ; 0.000317 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.05 |
Solubility : | 1.3 mg/ml ; 0.00899 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.47 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 3265 |
Hazard Statements: | H314 | Packing Group: | Ⅲ |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With hydroxylamine nitrate; sodium hydroxide In methanol at 0 - 50℃; for 3 h; | 44 g of sodium hydroxide (1.1 mol) was added portionwise at 0 to 10 ° C to a solution containing 53 g of hydroxylamine nitrate (0.55 mol) And 200 mL of methanol in the reaction flask. After all the addition of sodium hydroxide was added, the reaction was continued for 30 minutes. 79 g of methyl octanoate (0.5 mol) was added dropwise to the reaction flask over 30 minutes, and then the temperature was raised to 50 ° C and reacted for 2 hours. After the reaction, drop to the room Warm, filtered to obtain by-product of sodium nitrate, and then distilled to remove methanol (GC showed a small amount of methyl octanoate), the temperature dropped to 0 , And then slowly add 5percent nitric acid, adjust the pH value of 3 to 4, precipitation of solid, filter, filter cake dried octanoyl hydroxamic acid 67g, the yield 84percent |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With di-tert-butyl peroxide; copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 130℃; for 12 h; Sealed tube | General procedure: A 50 mL sealed tube (with a Teflon high pressure valve) equipped with a magnetic stir bar was charged with Cu(OTf)2 (0.05 mmol), followed by carboxylic acid (0.5 mmol), formamide (2.0 mmol), tert-butyl peroxide (DTBP, 1 mmol), and DCE (1 mL). After the reaction mixture was stirred at 130 °C for 12 h, it was allowed to cool to ambient temperature. The reaction mixture was diluted with ethyl acetate, and then filtered through a small pad of Celite. The filtrate was washed with saturated aqueous NaHCO3 (5 mL) and brine (5 mL, twice). The organic phase was dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel preparative TLC to give the corresponding product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | Stage #1: With 1,3,5-trichloro-2,4,6-triazine; triethylamine In dichloromethane at 0℃; for 0.5 h; Stage #2: at 0 - 25℃; for 1 h; |
General procedure: To a solution of 0.024 g TCT (0.130 mmol) in 2 cm3CH2Cl2 was added 0.033 g triethylamine (0.325 mmol) at0 C and the resulting mixture was stirred for 5 min.Carboxylic acid (0.271 mmol) was then added with continuouslystirring for 10 min. Subsequently, to this mixturewas added 0.032 g 1H-benzotriazole (0.271 mmol) and thesolution was allowed to warm up to room temperature andstirred until completion of the reaction based on TLCanalysis. The crude reaction mixture was extracted withsaturated NaHCO3, then washed with 1 M HCl and water.The combined organic layer was dried over anhydroussodium sulfate and concentrated under reduced pressure toafford the product. All known products were characterizedby 1H and 13C NMR and their spectroscopic data wereconsistent with those reported in literature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.81% | 29.13g n-octanoic acid (content 99%)And 21.05 g of acetic anhydride (content 97%) was added to the ball mill jar,Grinding for 10 min,Then add 14.11g hydroxylamine hydrochloride (content 98.5%),After continuing to grind for 40 minutes,Get a white solid product,It is the target collector product.After analysis and testing,The content of n-octyl hydroxydecanoic acid is 50.21%,Based on n-octanoic acidN-octyl hydroxamic acidThe yield was 95.81%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99.2% | With acetic acid; at 275℃; for 0.5h; | the caprylic acid, capric acid (caprylic acid boiling point 238 C, capric acid boiling point 270 C) mixed acid is gasified by a fatty acid pre-heater and from the bottom enter into the esterification kettle, so that acetic acid gas filling the kettle, the kettle temperature control at 275-280 C, then the catalyst and glycerol stirred in a premixed pot for 30 min, after that pass through the atomizer from the top of the bottle, and put the acetic acid into the kettle in the presence of atmospheric pressure, the reaction time will be 1h, during the reaction, the acetic acid gas is continuously passed, and it is ensure that the acid slightly overdose, and after the completion of the reaction, then stop the mixture of acid gas, continue reaction for 1h, and the reactant is discharged from the outlet. The product after esterification is colorless transparent oily liquid, acid value (mg KOH/g) is 0.06, decanoyl/octanoyl-triglycerides content 99.2%. |
93% | With tungsten(VI) oxide; at 175℃; under 1.0 Torr; for 22.0h; | Example 1 : Tricaprin (Capric acid: n = 8) [0040] To a 250-mL flask containing glycerol (5.0 g, 54.3 mmol) and equipped with a condenser, were added capric acid (37.4 g, 217.2 mmol) and calcium oxide (45.4 mg, 0.8 mmol). The mixture was heated at 175C under partial vacuum (1 Torr, water pump vacuum) for 22 hours. The temperature of the water in the condenser was approximately 35C in order to maintain a gentle reflux of the capric acid and to accelerate removal of water under vacuum. The reaction was cooled to room temperature and the residue dissolved in hot ethanol (95%, 400 mL). This solution was treated with charcoal, filtered over fiberglass and cooled in an ice bath at 0-5C for 2 hours. Tricaprin was crystallized as a white solid which was filtered and washed with cold ethanol (95%, 40 mL). Yield of product: 27.5 g (91 %); mp 29-31 C; 1H NMR (400 MHz, CDCI3): delta 5.22-5.29 (m, 1 H), 4.29 (dd, J = 1 1.9, J = 4.3, 2H), 4.14 (dd, J = 1 1.9, J = 6.1 , 2H), 2.26-2.34 (m, 6H), 1.54-1.65 (m, 6H), 1 .18-1.36 (m, 36H), 0.87 (t, J = 7.0, 9H). 13C NMR (101 MHz, CDCI3): delta 73.54, 173.13, 69.07, 62.32, 34.44, 34.27, 32.09, 29.67, 29.65, 29.51 , 29.50, 29.34, 29.30, 25.13, 25.08, 22.90, 14.33; MS (ES) m/z 578 (M+Na+); HPLC: 5.6 min; [0042] Triglyceride of caprylic acid was prepared as described in Example 1 by use of 1 1 g of caprylic acid (74.9 mmol), 1.7 g glycerol (18.7 mmol) and 15.7 mg calcium oxide (0.28 mmol). Since tricaprylin is a liquid, the crude product was filtered on silica gel, instead of fiberglass,using ethyl acetate/hexanes (5-10%). This gave the pure product as a colorless oil. Yield: 8 g (89%); H NMR (400 MHz, CDCI3): delta 5.25-5.28 (m, 1 H), 4. 29 (dd, J = 1 1 .9, J = 4.3,2H), 4.14 (dd, J = 1 1 .9, J = 6.1 , 2H), 2.28-2.34 (m, 6H), 1 .56-1 .66 (m, 6H), 1 .20-1.36 (m, 24H), 0.87 (t, J = 7.0, 9H). 13C (101 MHz, CDCI3): delta 173.56, 173.14, 69.07, 62.33, 34.45, 34.28, 31.89, 31.88, 29.28, 29.24, 29.16, 29.14, 25.13, 25.08, 22.83, 14.30; HPLC: 4.5 min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In di-isopropyl ether; for 1.5h;Inert atmosphere;Product distribution / selectivity; | To a solution of 6.0 g (35.0 mmol) <strong>[136236-51-6]rasagiline</strong> in 120 ml diisopropyl ether 5.5 ml (35.0 mmol, 1.0 eq) octanoic acid was added under nitrogen. After stirring for 90 min, the solvent was removed in vacuo at 3O0C. Drying on the rotary evaporator was continued for another 2 h at this temperature. Drying in high vacuum for 2 h yielded 10.9 g (34.6 mmol, 99 %) of a light brown oil.1H NMR (d6-DMSO, 300 MHz): delta = 7.31 (m, 1 H, PhH), 7.21-7.13 (m, 3 H, PhH), 4.25 (t, J = 6.3 Hz, 1 H, N-CH), 3.37 (d, J = 2.8 Hz, 2 H, N-CH2), 3.05 (t, J = 2.4 Hz, 1 H, alkynyl-H), 2.91 (m, 1 H, ring-CH), 2.74 (quint, J = 15.0, 7.5 Hz, 1 H, ring-CH), 2.28 (m, 1 H, ring-CH), 2.17 (t, J = 7.5 Hz, 2 H1 C(O)CH2), 1.76 (m, 1 H, ring-CH), 1.48 (bit, J = 6.9 Hz, 2 H, C(O)CH2CH2), 1.24 (S, 8 H, 4 x CH2), 0.85 (t, J = 6.3 Hz, 3 H, omega-CH3). The integrals confirm a ratio of amine/acid = 1 :1.IR: v = 2954.71 , 2927.69, 2855.59, 1713.63, 1607.76, 1548.75, 1459.54, 1401.97 cm"1. IR indicates protonation of the amine.HPLC (by area%): 99.58 %. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With recombinant esterase from Rhizomucor miehei; In aq. phosphate buffer; at 50℃; for 0.166667h;pH 6.5;Enzymatic reaction;Catalytic behavior; | General procedure: The substrate specificity for synthetic triacylglycerol esters was analyzed titrimetrically using 10 mM NaOH for titration according to the method of Egger et al. [37]. The substrates at a concentration of 10 mM were emulsified in 20 ml phosphate buffer (2.5 mM, pH 6.5) containing 1% arabic gum. The reaction was initiated with 10 mul of suitably diluted enzyme, and incubated at 50 C for 10 min, after which the reaction was titrated and the amount of consumed NaOH recorded. One unit of enzyme activity was defined as the amount of enzyme required to release 1.0 mumol of pNP or fatty acid per minute under the above assay conditions. | |
With Penicillium expansum lipase E83N mutant; polyvinyl alcohol; In aq. buffer; at 35℃; for 0.166667h;pH 9.0;Enzymatic reaction; | General procedure: The esterase activity was determined using p-nitrophenyl esters as substrates [7,8]. The lipolytic activity was evaluated titrimetrically using triacylglycerols with fatty acids of various chain lengths as substrates. 1 vol. of a certain triglyceride and 6 vol. of 2.0% (w/v) polyvinyl alcohol in 50mM glycine-NaOH buffer (pH 9.0) were mixed in a blender (10,000rpm) until homogeneity was achieved. Then, 9mL of this emulsified triglyceride was incubated with 1mL of suitably diluted enzyme at 35C for 10min and terminated by the addition of 15mL of ethanol. The release of fatty acids was monitored by titration using 50mM NaOH. One unit of lipolytic activity was defined as the amount of lipase necessary to produce 1mumol of fatty acid per minute under the above conditions. Interfacial activation was detected using p-nitrophenyl butyrate in a concentration range of 0.5-4.0mM. The temperature optima were determined under the conditions stated above, except that the reaction temperatures ranged from 25 to 45C. To detect thermostability, lipases were incubated at 30, 35, 40, 45, 50, and 55C for 10min, respectively. After incubation, residual enzymatic activity was measured using tributyrin as the substrate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 4 - 20℃; for 24.0h; | General procedure: PPT (500 mg) and different fatty acids (butyric acid, n-pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, capric acid, lauric acid, oleic acid, 8 mmol respectively) were dissolved in 25 mL dry tetrahydrofuran. N,N?-dicyclohexylcarbodiimide (DCC, 8 mmol) and 4-dimethylaminopyridine (DMAP, 0.8 mmol) were added while cooling on ice (4C). The mixture was stirred at room temperaturefor 24h, then was filtered, washed with CHCl3 three times and the filtrate combined. The filtrate was was evaporated to dryness under 80C to obtain the crude product. The crude product was subjected to silica gel column (3cm×40cm) chromatography, eluted with a gradient of petroleum and acetone (10:1-1.1) to obtain other compounds respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; at 20℃; for 6h; | Into 10 mL of chloroform were dissolved 75 mg (0.2 mmol) of <strong>[26687-82-1]arctigenin</strong> and 28.8 mg (0.2 mmol) of octanoic acid. Thereto were added 76.68 mg (0.4 mmol) of the water-soluble carbodiimide and 48 mg (0.4 mmol) of DMAP. In chloroform, the reactive components were caused to react with each other at room temperature for 6 hours. Water was added to the reaction liquid, and this system was stirred. The resultant organic layer was then washed with 1 N HCl, and a saturated solution of NaHCO3 in water. The chloroform layer was distilled off under a reduced pressure to yield <strong>[26687-82-1]arctigenin</strong> octanoate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Intermediate 39a: 10-(octanoyloxy)decanoic acid To a solution of octanoic acid (766 mg, 5.32 mmol) in dichloromethane (25 ml_) was added EDC.HCI (1.02g, 5.32 mmol) and DIPEA (0.95 ml_, 5.32 mmol). The reaction was stirred for 1 h at ambient temperature, then <strong>[1679-53-4]10-hydroxydecanoic acid</strong> (500 mg, 2.66 mmol) and DMAP (162 mg, 1.33 mmol) were added. The reaction was stirred for an additional 24h. The reaction was diluted with water, and the aqueous layer was extracted with dichloromethane (2 x 30ml_). the combined dichloromethane extracts were washed with brine, dried over sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the crude material was purified on silica gel with methanol / dichloromethane as eluent to provide the desired product. TLC (silica gel, 10% methanol in dichloromethane): Rf = 0.69 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With toluene-4-sulfonic acid; In neat (no solvent); at 60℃; for 4.0h; | General procedure: The FFA (2.0 g), glycerol formal (GlyF: 1.5 molar equivalent respect to the FFA) andp-toluene-sulfonic acid (5percent w/w respect of the weight of the FFA) were charged in a conventionalround bottom flask with a magnetic stirrer. The mixture was heated at 60 C and stirred vigorously for4 h. The reaction was quenched by neutralizing the acid catalyst with saturated solution of sodiumcarbonate then filtered. The liquid phase was collected in a separatory funnel and partitioned betweenchloroform and water (3 x 20 mL). The organic layer was dried over sodium sulfate, filtered and thesolvent eliminated using a rotary evaporator. The sample was stored in a glass vial Table 2 summarizesthe experimental conditions and the results of reactions between GlyF and the FFAs. (1,3-Dioxolan-4-yl)methyl octanoate (5) Liquid at RT; 1H-NMR (400 MHz, CDCl3) delta 4.35?3.41 (m, 4H),2.35 (ddd, J = 9.8, 6.6, 2.2 Hz, 2H), 1.63 (depth, J = 11.1, 3.5 Hz, 2H), 1.44 (s, 2H), 1.29 (d, J = 6.0 Hz, 9H),0.92?0.85 (m, 3H); 13C-NMR (100 MHz) delta 178.88, 95.12, 77.38, 68.26, 63.03, 33.95, 33.84, 31.32, 28.75,28.72, 28.58, 24.57, 24.39, 22.27, 13.73; GC-MS (relative intensity, 70 eV) m/z: 69 (5), 83 (5), 116 (5), 84 (6),109 (7), 42 (8), 58 (8), 73 (8), 126 (8), 128 (8), 98 (9), 103 (10), 45 (11), 87 (11), 145 (12), 146 (15), 41 (21),43 (21), 55 (26), 86 (68), 57 (77), 127 (100), 230 ([M]+, <1percent); IR (wavenumber cm-1; Transmittance percent)3558; 77, 2930; 32, 2858; 44, 1739; 32, 1492; 68, 1384; 61, 1166; 44, 1045; 55, 942; 64,757; 56. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14.19g | 4-Chloro-2-((2-chloro-4-nitrophenyl)carbamoyl)phenyl octanoate (61): To a dry 500 mL round-bottomed 3-neck flask equipped with thermometer and addition funnel under an argon atmosphere, was added CH2C12 (80 mL) and oxalyl chloride (7 mL, 0.083 mol). To the addition funnel was added CH2C12 (10 mL), DMF (0.5 mL), and octanoic acid (llmL, 0.069 mol) and this solution added drop-wise over 8 mm (rapid gas evolution). After addition was complete the reaction mixture was stirred at it for 2 hours. Dioxane (20 mL) was added and the flask was fitted with a distillation head. The reaction mixture was concentrated under house vacuum with heating (45-50C) to a volume between 10-15 mL. This concentrated mixture was then cooled to room temperature and dry THF (100 mL) was added. In a separate flask was added niclosamide (22.7 g, 0.069 mol), dry THF (200 mL) and to this suspension was added NEt3 (16 mL) and DIEA (10 mL). A majority of the solids dissolved and this mixture was added to the addition funnel, along with 10 mL of dry pyridine. Upon addition of the pyridine a precipitate formed that was suspended in an additional 150 mL of dry THF. This mixture was added to the solution of octanoyl chloride over a total of 15 min. As the niclosamide suspension was added to the acid chloride, the internal temperature began to increase to 28C at which point an ice-bath was provided to maintain the temperature between i5-25C during the addition. The resultant mixture was stirred over night at room temperature and monitored by HPLC and TLC (30% EtOAC/ hexane). The reaction mixture was poured into water and concentrated. The concentrate was diluted with CH2C12 and iN HC1 and the mixture filtered. The precipitate was washed with CH2C12 and the CH2C12 wash combined with the filtrate. The CH2C12 layers were combined and were washed three times with iN HC1, one time with brine, dried over Na2SO4, filtered and concentrated onto 25 mL of silica gel. The solids were eluted from a column of 200 mL of silica gel using a gradient of 7.8:2:0.2 to 7.5:2.5:0.2 hexane/chloroform/EtOAc. The fractions containing the desired compound were combined, heptane was added and the solution concentrated until a large volume of white precipitate was observed. The suspension was allowed to stand overnight, and the precipitate filtered, washed with hexane and dried under vacuum to yield i4. i9 g (32.5% over two steps) of the title compound as a white solid. ?H NMR (400 MHz, DMSOd6) oe iO.44 (s, iH), 8.40 (d, J 2.59 Hz, iH), 8.27 (dd, J= 9.03, 2.59 Hz, iH), 8.i3 (d, J= 9.08 Hz, iH), 7.82 (d, J 2.64 Hz, iH), 7.69 (dd, J= 8.69, 2.64 Hz, iH), 7.34 (d, J= 8.69 Hz, iH), 2.54 (t, J= 7.32 Hz, 2H), i.48 - i.59 (m, 2H), i.05 - i.28 (m, 8H), 0.79 (t, J 7.03 Hz, 3H). ?3C (i25 MHz, DMSO-d6) i7i.76, i63.67, i47.24, i44.75, i4i.22, i32.35, i30.6i, i30.42, i29.57, i27.24, i26.02, i25.89, i25.47, i23.53, 33.89, 3i.54, 28.87, 28.74, 24.59,22.50, i4.33. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84%; 3 g | With hydroxylamine nitrate; sodium hydroxide; In methanol; at 0 - 50℃; for 3h; | 44 g of sodium hydroxide (1.1 mol) was added portionwise at 0 to 10 C to a solution containing 53 g of hydroxylamine nitrate (0.55 mol) And 200 mL of methanol in the reaction flask. After all the addition of sodium hydroxide was added, the reaction was continued for 30 minutes. 79 g of methyl octanoate (0.5 mol) was added dropwise to the reaction flask over 30 minutes, and then the temperature was raised to 50 C and reacted for 2 hours. After the reaction, drop to the room Warm, filtered to obtain by-product of sodium nitrate, and then distilled to remove methanol (GC showed a small amount of methyl octanoate), the temperature dropped to 0 , And then slowly add 5% nitric acid, adjust the pH value of 3 to 4, precipitation of solid, filter, filter cake dried octanoyl hydroxamic acid 67g, the yield 84% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.8 eq of commercially available <strong>[204316-32-5]Fmoc-L-Dab(Alloc)-OH</strong> and DIEA (4 eq) are added to the resin in 2 mL DMF. The mixture is intermittently stirred manually during 1 hour. After that, 0.5 mL/g of MeOH are added to the reaction mixture to cap the remaining reactive points of resin. After 15 minutes, the solution is filtered off and the resin is washed thoroughly with DCM, DMF and MeOH. Fmoc removal is achieved by treating the resin with 20% piperidine in DMF (1 x 5', 1 x 10' and 1 x 15'). For the coupling of Fmoc-L-Ile-OH, 3 eq of the amino acid, 3 eq of the coupling agent TBTU and 6 eq of DIEA dissolved in a small amount of DMF and premixed for 2 minutes. After which, the mixture is added to the resin and the reaction is allowed to react for 90 minutes. To extent of the reaction is monitored using the Kaiser test. The Fmoc group is then removed by treatments with 20% piperidine in DMF (1 x 5', 1 x 10' and 1 x 15'). For the N-methylation of the amino group of the lle moiety, the free amino group is protected with ortho-nitro benzene sulfonyl chloride (4 eq) using collidine (10 eq) as a base in DMF, which are allowed to react with the resin for 30 minutes. Then, the resin is rinsed with DMF and DCM, and the protection step is repeated again under the same conditions. The extent of the protection is monitored using the Kaiser test. The N- methylation of the amino group is achieved by treating the resin with 3 eq of 7-methyl- l,5,7-triazabicyclo[4.4.0]dec-5-ene and 4 eq of para-nitrobencensulfonate in DMF for 30 minutes (3 treatments). Between treatments the resin is washed thoroughly with DMF and DCM. After the N-methylation of the IIe amino group, the ortho-nitro benzene sulfonyl protecting group is removed by treating the resin with 10 eq of beta- mercaptoethanol and 5 eq of DBU (1 x 10' and 1 x 40'). The removal of the ortho-nitro benzene sulfonyl group is assessed using the chloranil test. After that, the Fmoc-L-Pro- OH moiety is attached, for that purpose 3 eq of the amino acid, 3 eq of the coupling agent TBTU and 6 eq of DIEA dissolved in a small amount of DMF and premixed for 2 minutes. After which, the mixture is added to the resin and the reaction is allowed to react for 90 minutes. The extent of the reaction is monitored using the Kaiser test. The Fmoc group is then removed by treatments with 20% piperidine in DMF (1 x 5', 1 x 10' and 1 x 15') and additional treatment with a mixture of piperidine/DBU/toluene/DMF (5:5:20:70) (1 x 5'). Octanoic acid is coupled to the Pro moiety by adding to the resin 20 eq of the acid, 10 eq of the coupling regent DPCDI and 10 eq of the additive HO At. The reaction is stirred manually intermittently for 60 minutes. Then the reaction is filtered off and the resin is rinsed thoroughly with DMF and DCM. The extent of the reaction is monitored using the chloranil test. For the removal of the Alloc group, 10 eq of phenylsilane in DCM are added to the resin while N2 is bubbled through the mixture. Then, 0.1 eq of Pd(PPh3)4 are added maintaining the N2 bubbling while mixing everything well. Then the reaction vessel is sealed and shaken for 15 minutes. After this time, the reaction is filtered and the resin washed thoroughly. The same treatment is repeated two more times. After the last treatment, the resin is washed thoroughly with DCM, MeOH and DMF. For the coupling of the 3,5-difluorobenzoic acid on the side chain of the Dab moiety, 3 eq of said acid, 3 eq of TBTU and 6 eq of DIEA in DMF are added to the resin. The reaction is allowed to react for 60 minutes. After this time, the resin is washed with DMF and DCM and the extent of the reaction is monitored the Kaiser test. For the cleavage of the peptide, the resin is washed several times with DCM and dried by suction. The linear side-chain protected peptide is cleaved from the resin by adding a solution of HFIP/DCM (1 :4), the mixture is allowed to react for 15 min. Then the reaction mixture is filtered and the resin rinsed with HFIP/DCM. This cleavage procedure is repeated for a second time. All the filtrates are pooled and the solvent is evaporated under vacuum. The crude peptide is used for the formation of the hydroxamide in solution without prior purification. The peptide is dissolved in DCM. After which, 3.5 eq of 0-(2,4-dimethoxybenzyl)hydroxylamine, 5 eq of 4- methylmorpholine, 1.3 eq of the coupling agent EDC HCl and 1.3 eq of the additive HO At are added and the mixture is allowed to react under a N2 atmosphere overnight. The extent of the reaction is monitored using HPLC. Once the desired product is obtained, the mixture is washed with IN HC1, water and brine. The organic layer is dried over magnesium sulfate, filtered and evaporated. A mixture of TFA/water/TIS (95:2.5 :2.5) is added to the peptide crude and the mixture is lightly stirred during 2 hours. Afterwards, TFA is evaporated under a N2 flow, yielding example 6. The compound is purified using reverse-phase chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84.5% | 4 mmol was added to the reaction vesselOctanoic acid, 4 mmol of DCC, 4 mmol of DMAP, 20 mL of anhydrous DMA was added,Stirring under ice bath for 30 minutes;1 mmol of <strong>[38748-32-2]TP</strong> was dissolved in an appropriate amount of anhydrous methylene chloride and slowly added dropwise to the reaction system,Ice bath conditions for 45 minutes,The reaction was continued overnight at room temperature,The reaction was separated and purified by silica gel column to give 411.2 mg of <strong>[38748-32-2]triptolide</strong> octanoate. Yield 84.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21 g | With diisopropyl-carbodiimide; In tetrahydrofuran; at 0 - 25℃; | 20 g (0.048 mol) of N-fluorenylmethoxycarbonyl-L-serine-benzyl ester was dissolved in 260 ml of tetrahydrofuran until it was dissolved. Adding 11.2 g (0.0776 mol) of n-octanoic acid, The ice bath drops to 0 degrees Celsius. 7.78 g (0.0776 mol) of N,N'-diisopropylcarbodiimide was slowly added dropwise. N,N'-diisopropylcarbodiimide is dropped, Remove the ice bath, Let it slowly rise to 25 degrees Celsius and react overnight. The next day, After thin layer chromatography analysis, The raw material N-fluorenylmethoxycarbonyl-L-serine-benzyl ester has been completely reacted. Can be processed. Treatment: suction filtration of liquid, Slowly evaporate the tetrahydrofuran at 35 degrees Celsius. Get oil, The oil was dissolved in 400 ml of ethyl acetate. The ethyl acetate phase was washed twice with 5% by weight of citric acid water. After washing three times with water to pH = 7, it was washed once with brine and dried over anhydrous sodium sulfate. Filtering the liquid, Evaporate to dryness, 150 ml of petroleum ether was added to crystallize. Filtration to give the crude N-fluorenylmethoxycarbonyl-O-octanoyl-L-serine benzyl ester, Recrystallize again with ethyl acetate and petroleum ether. Obtaining a fine dry product of N-fluorenylmethoxycarbonyl-O-octanoyl-L-serine benzyl ester 21g; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20 g | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; at 0 - 25℃; | 20 g (0.046 mol) of <strong>[73724-48-8]N-fluorenylmethoxycarbonyl-L-threonine benzyl ester</strong> was dissolved in 250 ml of tetrahydrofuran. Until dissolved. Then add 10.7 g (0.0742 mol) of n-octanoic acid. The ice bath drops to 0 degrees Celsius. 14.2 g of 1-ethyl-(3-dimethylaminopropyl)carbonyldiimide hydrochloride was added in portions. Add 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, Remove the ice bath, Let it slowly rise to 25 degrees Celsius, The reaction was overnight. The next day, After thin layer chromatography analysis, The starting material N-fluorenylmethoxycarbonyl-L-threonine-benzyl ester has been completely reacted and can be processed. Treatment: suction filtration of liquid, Slowly evaporate the tetrahydrofuran at 35 degrees Celsius. Get oil, The oil was dissolved in 380 ml of ethyl acetate. The ethyl acetate phase was washed twice with 5% by weight of citric acid water. Wash three times with water until pH=7, Wash again with salt water, Dry over anhydrous sodium sulfate. Filtering the liquid, Evaporate to dryness, 140 ml of petroleum ether was added to crystallize. The crude N-fluorenylmethoxycarbonyl-3-O-octanoyl-L-threonine benzyl ester was obtained by suction filtration. Recrystallize again with ethyl acetate and petroleum ether. Get a boutique N-fluorenylmethoxycarbonyl-3-O-octanoyl-L-threonine benzyl ester dry weight product 20g; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; at 70℃; for 20h; | General procedure: The mixture of carboxylic acid, alcohol, and 1,3-dibromo-5,5-dimethylhydantoin was stirredin a 25 mL reactor tube at 70 C for 2-40 h. After reaction completion, the mixture was cooled toroom temperature and the alcohol was evaporated under reduced pressure. The isolation procedurewas as follows, except where noted dierently in the Supporting Information. The residue wasdissolved in 10 mL ethyl acetate and washed with a mixture of 1 mL saturated NaHCO3(aq), 1 mLsaturated Na2S2O3(aq), and 10 mL distilled water, and the water phase was extracted with ethyl acetate(2 10 mL). The organic layers were combined, dried over Na2SO4, and the solvent was evaporatedunder reduced pressure |
Tags: 124-07-2 synthesis path| 124-07-2 SDS| 124-07-2 COA| 124-07-2 purity| 124-07-2 application| 124-07-2 NMR| 124-07-2 COA| 124-07-2 structure
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