Structure of 89547-15-9
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| CAS No. : | 89547-15-9 |
| Formula : | C34H68O2 |
| M.W : | 508.90 |
| SMILES Code : | CCCCCCCCCCCCCCCCC(CCCCCCCCCCCCCCCC)C(O)=O |
| English Name : | 2-Hexadecyloctadecanoic acid |
| MDL No. : | MFCD00191519 |
* 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 |
|---|---|---|
| With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine In dichloromethane at 20℃; for 12h; | α-Branched chain fatty acid amides (T14, T14′16, and T16): General procedure: 100mmol of tris(2-aminoethyl)amine was poured in a flask. Then, 5mmol of the branched fatty acid (3a-c), 5mmol (benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate (PyBOP), and 5μL triethylamine (TEA) dissolved in 100mL CH2Cl2 were dropped into the solution under stirring. The mixture was stirred for further 12h at room temperature. The mixture was filtered and the organic solution was washed three times with water. The organic layer was separated, dried over Na2SO4, and evaporated. The crude product was purified by MPLC with CHCl3/MeOH/NH3 using gradient technique. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 3.7 g | With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 20℃; | 2.2 Step 2: Synthesis of tert-butyl 4-(2-hexadecyloctadecanoyloxy)phenylacetate After adding and dissolving 13.2 g of chloroform in 1.3 g (6.2 mmol) of tert-butyl 4-hydroxyphenylacetate,2-hexadecyl octadecanoic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) 3.0 g (5.9 mmol),DMAP (manufactured by Koei Chemical Co., Ltd.) 148 mg (1.3 mmol)and 1.3 g (6.8 mmol) of EDC hydrochloride (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the reaction was carried out at room temperature for 2 hours.The solution after the reaction was added once with 13.0 g of 0.1 mol/L hydrochloric acid,Once with 13.0 g of 5% sodium hydrogen carbonate aqueous solution,After washing once with 13.0 g of ion-exchanged water, it was concentrated using an evaporator.After adding 13g of hexane to the concentrate,260 mg of PSQ100B (manufactured by Fuji Silysia Chemical Co., Ltd.) was added and stirred at room temperature for 30 minutes.After separating PSQ100B by filtration, the filtrate was concentrated using an evaporator.The concentrate was vacuum-dried to obtain 3.7 g of tert-butyl 4-(2-hexadecyl octadecanoyloxy)phenylacetate (yield: 86 mol%/tert-butyl 4-hydroxyphenylacetate). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 25℃; | 13 Synthesis of compound 1 General procedure: Intermediate 4-a (187 mg), 2-hexyldecanoic acid (128 mg) and DMAP (12.0 mg) were dissolved in 2.81 g of chloroform at room temperature. EDC (144 mg) was added to the obtained solution, and the reaction was carried out at 25° C for 2 hours.After washing the reaction solution with 1.87 g of 20% by weight saline and removing sodium sulfate by filtration, the liquid was concentrated using an evaporator.The obtained crude product was purified using a column to obtain 159 mg of Compound 1. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 25℃; | 19 Synthesis of compound 1 General procedure: Intermediate 4-a (187 mg), 2-hexyldecanoic acid (128 mg) and DMAP (12.0 mg) were dissolved in 2.81 g of chloroform at room temperature. EDC (144 mg) was added to the obtained solution, and the reaction was carried out at 25° C for 2 hours.After washing the reaction solution with 1.87 g of 20% by weight saline and removing sodium sulfate by filtration, the liquid was concentrated using an evaporator.The obtained crude product was purified using a column to obtain 159 mg of Compound 1. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 25℃; | 20 Synthesis of compound 1 General procedure: Intermediate 4-a (187 mg), 2-hexyldecanoic acid (128 mg) and DMAP (12.0 mg) were dissolved in 2.81 g of chloroform at room temperature. EDC (144 mg) was added to the obtained solution, and the reaction was carried out at 25° C for 2 hours.After washing the reaction solution with 1.87 g of 20% by weight saline and removing sodium sulfate by filtration, the liquid was concentrated using an evaporator.The obtained crude product was purified using a column to obtain 159 mg of Compound 1. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 25℃; | 11 Synthesis of compound 1 General procedure: Intermediate 4-a (187 mg), 2-hexyldecanoic acid (128 mg) and DMAP (12.0 mg) were dissolved in 2.81 g of chloroform at room temperature. EDC (144 mg) was added to the obtained solution, and the reaction was carried out at 25° C for 2 hours.After washing the reaction solution with 1.87 g of 20% by weight saline and removing sodium sulfate by filtration, the liquid was concentrated using an evaporator.The obtained crude product was purified using a column to obtain 159 mg of Compound 1. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 25℃; | 12 Synthesis of compound 1 General procedure: Intermediate 4-a (187 mg), 2-hexyldecanoic acid (128 mg) and DMAP (12.0 mg) were dissolved in 2.81 g of chloroform at room temperature. EDC (144 mg) was added to the obtained solution, and the reaction was carried out at 25° C for 2 hours.After washing the reaction solution with 1.87 g of 20% by weight saline and removing sodium sulfate by filtration, the liquid was concentrated using an evaporator.The obtained crude product was purified using a column to obtain 159 mg of Compound 1. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 25℃; | 38 Synthesis of intermediate 31 Intermediate 30 (1.40 g), 2-hexadecyl octadecanoic acid (1.80 g) and DMAP (79.0 mg) were dissolved in 21.0 g of chloroform at room temperature.EDC (925 mg) was added to the obtained solution, and the reaction was carried out at 25° C. for 2 hours.The reaction solution was concentrated using an evaporator to obtain 2.98 g of crude intermediate 31. | |
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 25℃; | 38 Synthesis of intermediate 31 Intermediate 30 (1.40 g), 2-hexadecyl octadecanoic acid (1.80 g) and DMAP (79.0 mg) were dissolved in 21.0 g of chloroform at room temperature. EDC (925 mg) was added to the obtained solution, and the reaction was carried out at 25° C. for 2 hours. The reaction solution was concentrated using an evaporator to obtain 2.98 g of crude intermediate 31. | |
| With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In chloroform at 25℃; | 38 Synthesis of intermediate 31 Intermediate 30 (1.40 g), 2-hexadecyl octadecanoic acid (1.80 g) and DMAP (79.0 mg) were dissolved in 21.0 g of chloroform at room temperature. EDC (925 mg) was added to the obtained solution, and the reaction was carried out at 25° C. for 2 hours. The reaction solution was concentrated using an evaporator to obtain 2.98 g of crude intermediate 31. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 1.44 g | Stage #1: 2-hexadecyloctadecanoic acid With thionyl chloride In N,N-dimethyl-formamide at 60℃; for 2h; Stage #2: 3-(trimethoxysilyl)-N-[3-(trimethoxysilyl)propyl]-1-propanamine With triethylamine In N,N-dimethyl-formamide; toluene for 18h; | 7 Synthesis Example 7 Thionyl chloride (2.8 g) and dimethylformamide (1 drop) were added to 2-hexadecyloctadecanoic acid (1 g), and the mixture was stirred at 60° C. for 2 hours and then concentrated under reduced pressure. Toluene (10 mL), triethylamine (0.22 g), and bis[3-(trimethoxysilyl)propyl]amine (0.74 g) were added to the residue, and the mixture was stirred for 18 hours. Chloroform was added, and the mixture was washed three times with water. The organic layer was then dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain {CH3(CH2)15}2CCONHCH2CH2CH2Si(OCH3)3(compound a-7, 1.44 g, colorless liquid). |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 65% | With tert.-butylhydroperoxide; Duroquinone; palladium diacetate; C24H15F9N4O2; C4H12N(1+)*C2H3O2(1-)*H2O; potassium hydroxide In decane; 1,1,1,3',3',3'-hexafluoro-propanol; acetonitrile at 105℃; for 20h; Sealed tube; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 64% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; | |
| 64% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; | 1.1 C18-0-B' 2-Hexadecylooctadecanoic acid (0.20 g, 0.39 mmol, 2.0 eq) was dissolved in 10 mL of DCM. Triethanolamine (28 mg, 0.20 mmol, 1.0 eq) and DMAP (48 mg, 0.39 mmol, 2.0 eq) were added. The mixture was then stirred at 0 °C. DCC (80 mg, 0.39 mmol, 2.0 eq) was dissolved in 5 mL of DCM and added dropwise to the solution. The mixture was stirred overnight. After TLC showed the reaction was complete, the residue was removed by filtration. The mixture was then evaporated and purified by column chromatography (DCM/MeOH = 15/1). The desired product (0.28 g, 64% yield) was obtained. |