Stage #1: With sodium hydride In tetrahydrofuran; mineral oil for 1 h; Inert atmosphere; Cooling with ice Stage #2: at 20℃; for 1 h; Inert atmosphere; Cooling with ice
Sodium hydride (60percent dispersion) (21.0 g) and THF (200 ml) were added to a reaction container equipped with a stirrer and a thermometer in a nitrogen atmosphere, and the mixture was stirred under ice cooling, and a THF (100 ml) solution of the compound (S-14) (20.0 g) was slowly added dropwise thereto. After stirring for 1 hour after the dropwise addition, 1-chloroethanol (23.3 g) was added dropwise thereto under ice cooling, the temperature was gradually raised to room temperature and stirring was carried out for 1 hour. After stopping the reaction by adding water (200 ml), the organic layer was collected, the aqueous layer was extracted with THF (100 ml) four times, the resulting THF was mixed with the organic layer obtained above and washed with 5percent aqueous sodium hydroxide solution (400 ml) and subsequently with saturated saline (400 ml), dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was distilled under reduced pressure to obtain a compound (5-15) (31.2 g).
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5 h; Inert atmosphere Stage #2: at 20℃; for 12 h; Inert atmosphere Stage #3: With sulfuric acid; water In tetrahydrofuran for 3 h; Inert atmosphere; Reflux
(Using the synthesis of M-PEG 7 as an example). Under the atmosphere of N2, to a suspension of NaH (1.0 g, 60percent dispersed in mineral oil, 25.0 mmol) in THF (60 mL) at 0 was added a solution of M-PEG 5 (2.0 g, 16.6 mmol) in THF (20 mL). After the addition, the stirring mixture was warmed to rt and stirred for 30 min. Then, a solution of macrocyclic sulfate 8 (5.1 g, 20.0 mmol) in THF (20 mL) was added. The resulting mixture was stirred for 12 h at rt, and concentrated under vacuum. The resulting residue was dissolved in water (50 mL), and washed with CH2Cl2. The aqueous layer was concentrated and then dissolved in THF (100 mL). Then, water (0.6 mL, 33.3 mmol) and H2SO4 (0.4 mL, 8.4 mmol) were added to the reaction mixture and the resulting mixture was refluxed for 3 h. The reaction was neutralized with saturated NaHCO3 solution, extracted with CH2Cl2. The organic layers were dried over anhydrous Na2SO4, concentrated under vacuum, and purified by flash chromatography on silica gel (CH2Cl2/MeOH = 20/1) to give M-OEG 7 as clear oil (4.3 g, 88percent yield). 1H NMR (400 MHz, CDCl3) δ 3.73-3.70 (m, 2H), 3.70-3.63 (m, 18H), 3.62-3.59 (m, 2H), 3.57-3.55 (m, 2H), 3.39 (s, 3H).
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[1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 22, p. 3502 - 3505
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[ 111-77-3 ]
[ 23601-40-3 ]
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[1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 9, p. 1357 - 1360
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[ 111-77-3 ]
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[3] Collection of Czechoslovak Chemical Communications, 1976, vol. 41, # 4, p. 1248 - 1252
[4] Journal of Medicinal Chemistry, 1995, vol. 38, # 7, p. 1067 - 1083
[5] Tetrahedron Letters, 2007, vol. 48, # 28, p. 4813 - 4815
[6] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 7, p. 1381 - 1384
[7] Patent: US2017/253569, 2017, A1, . Location in patent: Paragraph 1254-1255
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[1] J. Gen. Chem. USSR (Engl. Transl.), 1970, vol. 40, p. 1598 - 1602[2] Zhurnal Obshchei Khimii, 1970, vol. 40, # 7, p. 1611 - 1616
[3] Patent: US4408075, 1983, A,
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[ 70384-51-9 ]
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[1] Journal of Organic Chemistry, 1985, vol. 50, # 20, p. 3717 - 3721
[2] Journal of Organic Chemistry, 1985, vol. 50, # 20, p. 3717 - 3721
Stage #1: With phthalimide; triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 20℃; Stage #2: With hydrazine hydrate In ethanolReflux
Diethylene glycol monomethyl ether (3.9 mL, 33.3 mmol) and diethyl azodicarboxylate (2.2 mol/L toluenesolution) (15.5 mL, 34.1 mmol) were added to a solution of phthalimide (4.90 g, 34.2 mmol) and triphenylphosphine(9.00 g, 34.2 mmol) in tetrahydrofuran (180 mL) at room temperature, and stirred overnight. To the resulting solution,ethanol (60 mL) was further added, stirred at room temperature for 30 minutes, and then the solvent was distilled awayunder a reduced pressure. Ethyl acetate (50 mL) and hexane (50 mL) were added to the residue, and insolubles werefiltered off. After the filtrate was concentrated under a reduced pressure, ethanol (120 mL) and hydrazine monohydrate(2.4 mL, 68.6 mmol) were added, and stirred under heat reflux overnight. After this solution was cooled to room temperature,concentrated hydrochloric acid (15 mL) was added, and stirred under heat reflux for 1 hour. After this solutionwas cooled to room temperature, insolubles were filtered off, and the filtrate was concentrated under a reduced pressure.Water was added to the residue, which was washed with diethyl ether. The aqueous layer was adjusted to pH = 13 witha 3N sodium hydroxide aqueous solution, and extraction was carried out with dichloromethane. The organic layer wasdried with anhydrous sodium sulfate, the solvent was distilled away under a reduced pressure to obtain the title compound(1.74 g, 44percent) as a pale yellow oily matter.1H NMR (400 MHz, CDCl3) δ 3.64-3.61 (2H, m), 3.57-3.55 (2H, m), 3.51 (2H, t, J = 5.2 Hz), 3.39 (3H, s), 2.89-2.87 (2H, m).
Reference：
[1] Patent: EP3127900, 2017, A1, . Location in patent: Paragraph 0142; 0143
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 7, p. 1381 - 1384
[3] Journal of the American Oil Chemists' Society, 1996, vol. 73, # 1, p. 79 - 86
[4] Journal of Medicinal Chemistry, 1995, vol. 38, # 7, p. 1067 - 1083
[5] Journal of the American Chemical Society, 1994, vol. 116, # 12, p. 5057 - 5062
[6] J. Gen. Chem. USSR (Engl. Transl.), 1970, vol. 40, p. 1598 - 1602[7] Zhurnal Obshchei Khimii, 1970, vol. 40, # 7, p. 1611 - 1616
[8] Chemische Berichte, 1979, vol. 112, p. 1392 - 1399
[9] Journal of Organic Chemistry, 2011, vol. 76, # 6, p. 1683 - 1691
[10] Angewandte Chemie - International Edition, 2012, vol. 51, # 5, p. 1152 - 1155
[11] Patent: EP2439204, 2012, A1,
[12] Macromolecules, 2012, vol. 45, # 12, p. 5151 - 5156
[13] Inorganica Chimica Acta, 2016, vol. 452, p. 159 - 169
[14] Journal of the American Chemical Society, 2017, vol. 139, # 17, p. 6234 - 6241
[15] MedChemComm, 2017, vol. 8, # 3, p. 662 - 672
[16] Patent: WO2009/109035, 2009, A1,
Stage #1: With sodium In tetrahydrofuran at 0 - 20℃; for 24 h; Inert atmosphere Stage #2: for 5 h;
PREPARATION EXAMPLE 4 Synthesis of 3-[2-(2-methoxyethoxy)ethoxy]propanoic acid To a 500 mL four neck flask purged with argon, 110 mL (0.93 mol) of 2-(2-methoxyethoxy)ethanol and 50 mL of dehydrated THF were added. After cooling to 0° C., 1.4 g (0.06 mol) of sodium metal was added thereto. After confirming no gas generation from the resulting reaction solution, a solution in which 44 mL (0.31 mol) of tertiary butyl acrylate is diluted in 50 mL of THF was slowly added dropwise thereto. Once the dropwise addition is completed, the reaction solution was heated from 0° C. to room temperature and then stirred for 24 hours at room temperature. The resulting reaction solution was dried under reduced pressure for removing THF by distillation. Then, 100 mL (0.3 mol) of 3 mol/L aqueous solution of sodium hydroxide was added and stirred for 5 hours. After adjustment to have pH=2 by adding 10percent aqueous solution of sulfuric acid to the obtained reaction solution, extraction was performed three times by using methylene chloride. The obtained organic layer was dried over anhydrous magnesium sulfate and dried under reduced pressure. The obtained crude 3-[2-(2-methoxyethoxy)ethoxy]propanoic acid was distilled twice under reduced pressure at 140° C., 0.1 kPa to obtain 14 g of 3-[2-(2-methoxymethyl)ethoxy]propanoic acid (yield: 24percent). 1H-NMR analysis data of the obtained 3-[2-(2-methoxyethoxy)ethoxy]propanoic acid is given below. 1H-NMR(DMSO-d6) δ(ppm)=2.67(q,2H), 2.51(q,2H), 2.07(s,3H)
With carbon tetrabromide; triphenylphosphine; In tetrahydrofuran; at 0 - 20℃; for 16h;
Step 1. Synthesis of 1-bromo-2-(2-methoxyethoxy)ethane To a solution of diethylene glycol monomethyl ether (0.698 g, 5.81 mmol) in THF (10 mL) was added triphenylphosphine (1.53 g, 5.83 mol) and carbon tetrabromide (1.93 g, 5.81 mol) at 0 C. After the solution was stirred at room temperature for 16 h, it was quenched with saturated NaHCO3(aq) and extracted with CH2Cl2. The combined organic layers were dried over MgSO4(s), filtered, and concentrated. The residue was purified by flash chromatography (20% ethyl acetate in n-hexane) to give 1-bromo-2-(2-methoxyethoxy)ethane as a yellow liquid. 1H NMR (CDCl3, 300 MHz) delta 3.81 (t, 2H), 3.68-3.65 (m, 2H), 3.57-3.54 (m, 2H), 3.48 (t, 2H), 3.39 (s, 3H).
Diethylene glycol monomethyl ether (3.9 mL, 33.3 mmol) and diethyl azodicarboxylate (2.2 mol/L toluenesolution) (15.5 mL, 34.1 mmol) were added to a solution of phthalimide (4.90 g, 34.2 mmol) and triphenylphosphine(9.00 g, 34.2 mmol) in tetrahydrofuran (180 mL) at room temperature, and stirred overnight. To the resulting solution,ethanol (60 mL) was further added, stirred at room temperature for 30 minutes, and then the solvent was distilled awayunder a reduced pressure. Ethyl acetate (50 mL) and hexane (50 mL) were added to the residue, and insolubles werefiltered off. After the filtrate was concentrated under a reduced pressure, ethanol (120 mL) and hydrazine monohydrate(2.4 mL, 68.6 mmol) were added, and stirred under heat reflux overnight. After this solution was cooled to room temperature,concentrated hydrochloric acid (15 mL) was added, and stirred under heat reflux for 1 hour. After this solutionwas cooled to room temperature, insolubles were filtered off, and the filtrate was concentrated under a reduced pressure.Water was added to the residue, which was washed with diethyl ether. The aqueous layer was adjusted to pH = 13 witha 3N sodium hydroxide aqueous solution, and extraction was carried out with dichloromethane. The organic layer wasdried with anhydrous sodium sulfate, the solvent was distilled away under a reduced pressure to obtain the title compound(1.74 g, 44%) as a pale yellow oily matter.1H NMR (400 MHz, CDCl3) delta 3.64-3.61 (2H, m), 3.57-3.55 (2H, m), 3.51 (2H, t, J = 5.2 Hz), 3.39 (3H, s), 2.89-2.87 (2H, m).
EXAMPLE 3 Preparation of tris-(3,6-dioxa-heptyl)amine of the formula: The operation described in Example 1 was carried out starting with 7500 g. of Raney nickel, 25,000 g. of 3,6-dioxa-1-heptanol, 1700 g. per hour of ammonia, and 50 g. per hour of hydrogen. The conversion rate of the ether alcohol was 90 percent.
EXAMPLE 9 Preparation of N-(4-Methoxyphenyl)-1,2-ethanediamine A mixture of 4-methoxyaniline hydrochloride (17.1 g, 0.107 mole), 2-oxazolidinone (8.7 g, 0.10 mole) and 50 ml of 2-(2-methoxyethoxy)ethanol was heated to 175 C. After five hours, carbon dioxide gas evolution had ceased and the dark mixture was allowed to cool to room temperature. Neutralization in a manner similar to that described in Example 1, and distillation at 130 C. to 140 C. (0.5 mm Hg) afforded a 45 percent yield of the amine as a colorless liquid which slowly solidified on standing at ambient temperature to a low-melting solid.
With caesium carbonate; In N,N-dimethyl-formamide; at 90℃;
Step 4 - Preparation of2-chloro-5-fluoro-4-[2-(2-methoxy-ethoxy)-ethoxy]-benzaldehyde (121) [0183] To <strong>[165047-23-4]2-chloro-4,5-difluoro-benzaldehyde</strong> (110, 0.40 g, 0.0023 mol) in N1N- dimcthylformamide (10.0 mL), 2-(2-methoxyethoxy)-ethanol (0 327 g, 2 72 mmol) and cesium carbonate (0.886 g, 2.72 mmol) were added. The reaction was stirred at 90 0C overnight The reaction was poured into water, acidified to pH around 5, and extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate and filtered The filtrate was concentrated and purified by silica gel column chromatography elutmg with 30% ethyl acetate in hexane to give a white solid (121, 0.15 g, 24.C
Example 15: Synthesis of 2-chloro-5-fluoro-4-hydroxy-benzaldehyde 111.[0184] 2-Chloro-5-fiuoro-4-hydroxy-benzaldehyde 111 was synthesized in one step from 2-chloro- 4,5-difluoro-bcnzaldchydc 110 as shown in Scheme 37.Step 1 - Preparation of2-chloro-5-fluoro-4-hydroxy-benzaldehyde (111)[0185] To <strong>[165047-23-4]2-chloro-4,5-difluoro-benzaldehyde</strong> (110, 0.40 g, 2.30 mmol, prepared as described in Example 14) in N,N-dimethylformamide (10 0 mL) were added 2-(2-methoxyethoxy)-ethanol, (0 327 g, 2 72 mmol) and cesium carbonate (0 886 g, 2 72 mmol) The reaction was stirred at 90 0C overnight The reaction was poured into water, acidified to pH around 5, and extracted with ethyl acetate The organic layer was dried over anhydrous sodium sulfate and filtered The filtrate was concentrated and purified by silica gel column chromatography elutmg with 30% ethyl acetate in <n="79"/>hexane to give a white solid (111. 0 24 g, 61 0%) MS (ESI) [M-H"] = 173 1
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 48h;
2-(2-Methoxyethoxy)ethanol (0.309 mL, 2.60 mmol), triphenylphosphine (0.681 g, 2.60 mmol) and diisopropyl azodicarboxylate (0.511 mL, 2.60 mmol) were added to a solution of <strong>[106291-80-9]methyl 4-bromo-3-hydroxybenzoate</strong> (0.4 g, 1.7 mmol) in tetrahydrofuran (20 mL) and the reaction mixture was stirred at room temperature for 2 days. A solution of lithium hydroxide monohydrate (0.124 g, 5.19 mmol) in water (2 mL) was added and the reaction mixture was stirred for another 4 days. The reaction mixture acidified with 2.0 M aqueous hydrochloric acid and partitioned between water and ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent was evaporated. The product 4-bromo-3-(2-(2-methoxyethoxy)ethoxy)benzoic acid (0.562 g, 1.76 mmol), N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (0.506 g, 2.64 mmol) and 4-dimethylaminopyridine (0.323 g, 2.64 mmol) were added to a solution of benzene-1,2-disulfonamide (0.546 g, 2.31 mmol) in N,N-dimethylformamide (30 mL) at room temperature and stirred over night. Water was added and the solution was extracted with ethyl acetate. The aqueous phase was acidified with 2 M aqueous hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by column chromatography, using ethyl acetate/methanol (50:1+1% triethylamine) as the eluent, gave 0.55 g (60% yield) of the title compound.1H NMR (400 MHz, CD3OD) delta ppm 8.45-8.55 (m, 1H), 8.22-8.31 (m, 1H), 7.81-7.89 (m, 2H), 7.62 (d, 1H), 7.53 (d, 1H), 7.35 (dd, 1H), 4.18-4.29 (m, 2H), 3.83-3.91 (m, 2H), 3.72 (dd, 2H), 3.51-3.58 (m, 2H), 3.27-3.35 (m, 3H); MS (ES) m/z 435 and 437 [M-1]-.
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃; for 48h;
2-(2-Methoxyethoxy)ethanol (0.309 mL, 2.60 mmol), triphenylphosphine (0.681 g, 2.60 mmol) and diisopropyl azodicarboxylate (0.511 mL, 2.60 mmol) were added to a solution of <strong>[106291-80-9]methyl 4-bromo-3-hydroxybenzoate</strong> (0.4 g, 1.7 mmol) in tetrahydrofuran (20 mL) and the reaction mixture was stirred at room temperature for 2 days. A solution of lithium hydroxide monohydrate (0.124 g, 5.19 mmol) in water (2 mL) was added and the reaction mixture was stirred for another 4 days. The reaction mixture acidified with 2.0 M aqueous hydrochloric acid and partitioned between water and ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent was evaporated. The product 4-bromo-3-(2- (2-methoxyethoxy)ethoxy)benzoic acid (0.562 g, 1.76 mmol), N-(3-dimethylaminopropyl)- N'-ethylcarbodiimide hydrochloride (0.506 g, 2.64 mmol) and 4-dimethylaminopyridine (0.323 g, 2.64 mmol) were added to a solution of benzene- 1 ,2-disulfonamide (0.546 g, 2.31 mmol) in N,N-dimethylformamide (30 mL) at room temperature and stirred over night.Water was added and the solution was extracted with ethyl acetate. The aqueous phase was acidified with 2 M aqueous hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent was evaporated. Purification by column chromatography, using ethyl acetate/methanol (50:1 + 1% triethylamine) as the eluent, gave 0.55 g (60% yield) of the title compound.1H NMR (400 MHz, CD3OD) delta ppm 8.45 - 8.55 (m, 1 H), 8.22 - 8.31 (m, 1 H), 7.81 - 7.89 (m, 2 H), 7.62 (d, 1 H), 7.53 (d, 1 H), 7.35 (dd, 1 H), 4.18 - 4.29 (m, 2 H), 3.83 - 3.91 (m, 2 H), 3.72 (dd, 2 H), 3.51 - 3.58 (m, 2 H), 3.27 - 3.35 (m, 3 H); MS (ES) m/z 435 and 437 [M-I]-.
PREPARATION EXAMPLE 4 Synthesis of 3-[2-(2-methoxyethoxy)ethoxy]propanoic acid To a 500 mL four neck flask purged with argon, 110 mL (0.93 mol) of 2-(2-methoxyethoxy)ethanol and 50 mL of dehydrated THF were added. After cooling to 0 C., 1.4 g (0.06 mol) of sodium metal was added thereto. After confirming no gas generation from the resulting reaction solution, a solution in which 44 mL (0.31 mol) of tertiary butyl acrylate is diluted in 50 mL of THF was slowly added dropwise thereto. Once the dropwise addition is completed, the reaction solution was heated from 0 C. to room temperature and then stirred for 24 hours at room temperature. The resulting reaction solution was dried under reduced pressure for removing THF by distillation. Then, 100 mL (0.3 mol) of 3 mol/L aqueous solution of sodium hydroxide was added and stirred for 5 hours. After adjustment to have pH=2 by adding 10% aqueous solution of sulfuric acid to the obtained reaction solution, extraction was performed three times by using methylene chloride. The obtained organic layer was dried over anhydrous magnesium sulfate and dried under reduced pressure. The obtained crude 3-[2-(2-methoxyethoxy)ethoxy]propanoic acid was distilled twice under reduced pressure at 140 C., 0.1 kPa to obtain 14 g of 3-[2-(2-methoxymethyl)ethoxy]propanoic acid (yield: 24%). 1H-NMR analysis data of the obtained 3-[2-(2-methoxyethoxy)ethoxy]propanoic acid is given below. 1H-NMR(DMSO-d6) delta(ppm)=2.67(q,2H), 2.51(q,2H), 2.07(s,3H)
With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 48h;
Diethylene glycol monomethyl ether (20g, 170mmol) and sodium hydride (4g, 170mmol) in anhydrous tetrahydrofuran until no bubbles, and then at 0 3- methyl-3- (p-toluenesulfonic acid methyl ester) oxetane (43g, 170mmol) was added dropwise to the reaction system, the reaction was added dropwise at room temperature 48 hours after recovery.After the reaction, the reaction solution was diluted with water, and extracted by dichloromethane, distilled under reduced pressure to give a colorless liquid.Yield: 65%.1
With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 48h;
Diethylene glycol monomethyl ether (20g, 170mmol) and sodium hydride (4g, 170mmol) in anhydrous tetrahydrofuran until no bubbles, and then at 0 3- (methyl tosylate) oxy oxetane (41.2g, 170mmol) was added dropwise to the reaction system, the reaction was added dropwise at room temperature 48 hours after recovery.After the reaction, the reaction solution was diluted with water and extracted by dichloromethane, distilled under reduced pressure to give a colorless liquid.Yield: 70%
ricinoleic acid diethylene glycol monomethyl ether ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
96%
With sodium hydrogensulfate monohydrate; In dichloromethane; at 150℃; for 0.416667h;Microwave irradiation; High pressure;
General procedure: <strong>[141-22-0]Ricinoleic acid</strong> (10.0 mmol) 1a, glycol ethers 2a-2i (12.0 mmol) and DCM (5.0 mL), and NaHSO4 · H2O (0.01% mol) were added into a dry 10.0-mL microwave reaction tube, which was put into a microwave reactor. The desired product was afforded after 25 min at 150 C (Scheme 2). The reaction progress was followed by a thin-layer chromatography and the crude product was purified on column chromatography of silica gel using ethyl acetate-petroleum ether (1:7) as eluent. All products were characterized by 1H NMR, 13C NMR, FTIR, and high resolution mass spectrometer (HRMS), and spectrum data of 3a-3i were listed.
4,6-dichloro-2-(2-(2-methoxyethoxy)ethoxy)pyrimidine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
60%
Under nitrogen, sodium hydride (1 eq)And 2- (2-methoxyethoxy) ethanol (1 eq)Is added to the anhydride THF and stirred for 1 hour in an ice bath. Then, 4,6-dichloro-2-methanesulfonyl-pyrimidine (1.5 eq) is dissolved in THF and stirred overnight.After completion of the reaction, the solvent was dried with a rotary evaporator, and the EA layer was separated from the separatory funnel by using NaHCO 3 solution / EA and dried by drying with MgSO 4. Filter solution was removed by rotary evaporator and column. Yield: white oil 60%.
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