123770-62-7 | Page 3 of 3 | Heterocyclic Building Blocks-isoxazole

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.123770-62-7,Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate,as a common compound, the synthetic route is as follows.

123770-62-7, 6.2. tert-Butyl (3aR,5r,6aS)-5-{2-[({[3-(ethoxycarbonyl)-isoxazol-5-yl]methoxy}carbonyl)amino]ethyl}hexahydrocyclo-penta[c]pyrrole-2(1H)-carboxylate; Added slowly to a solution of 0.33 g (1.97 mmol) of ethyl 5-hydroxymethylisoxazole-3-carboxylate and 0.34 ml (1.97 mmol) of N,N-diisopropylethylamine in 10 ml of 1,2-dichloroethane, cooled to 0 C., is 0.43 g (2.16 mmol) of p-nitrophenyl chloroformate in solution in 5 ml of dichloroethane. The mixture is then stirred at room temperature for 2 hours then a solution of 0.5 g (1.97 mmol) of tert-butyl (3aR,5r,6aS)-5-(2-aminoethyl)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate, obtained in step 6.1., and 0.34 ml (1.97 mmol) of N,N-diisopropylethylamine are added. The mixture is then heated at 70 C. for 3 hours.After returning to room temperature, water is added then the aqueous phase is extracted several times with dichloromethane. The combined organic phases are then successively washed with a 1M aqueous solution of sodium hydroxide (three times) then with a saturated aqueous solution of ammonium chloride (twice). The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. After purification on a silica gel column eluting with a 99/1 then 97/3 mixture of dichloromethane and methanol, 0.44 g of pure product is obtained in the form of an orange oil.LC-MS: M+H=4521H NMR (DMSO) delta(ppm): 7.40 (broad s, 1H), 6.36 (s, 1H), 5.19 (s, 2H), 4.37 (q, 2H), 3.32 (m, 2H), 3.08 (m, 2H), 2.98 (m, 2H), 2.52 (m, 2H), 2.00 (m, 2H), 1.83 (m, 1H), 1.46 (m, 2H), 1.38 (s, 9H), 1.32 (t, 3H), 0.90 (m, 2H).

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Reference£º
Patent; SANOFI; US2012/136026; (2012); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Some tips on 123770-62-7

123770-62-7 Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate 8027233, aIsoxazoles compound, is more and more widely used in various fields.

123770-62-7, In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), commercially available 5-hydroxymethyl-isoxazole-3-carboxylic acid ethyl ester (5.00 g, 26.29 mmol) was dissolved in dry THF (200 ml_). te/t-Butyldimethylsilyl chloride (4.04 g, 26.82 mmol) was added at rt followed by imidazole (1.97 g, 28.92 mmol). The reaction mixture was stirred at rt overnight. Sat. aq. NH4CI (150 ml.) was added followed by EA (100 ml.) and the layers were separated. The aq. layer extracted with EA (2 x 100 ml_). The combined org. extracts were dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (9:1 hept-EA) gave the title compound as a light yellow oil: TLC: rf (9:1 hept-EA) = 0.37. LC-MS-conditions 02: tR = 1.14 min; [M+AcCN+H]+ = 327.51.

123770-62-7 Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate 8027233, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; ACTELION PHARMACEUTICALS LTD; WO2009/77990; (2009); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

New learning discoveries about 123770-62-7

As the paragraph descriping shows that 123770-62-7 is playing an increasingly important role.

Reference Production Example 200 (0843) Ethyl 5-hydroxymethylisoxazole-3-carboxylate (0.72 g, 4.2 mmol) was dissolved in tetrahydrofuran (25 mL), and 1-fluoro-2-naphthylmethyl bromide (1.20 g, 5.0 mmol) and 18-crown-6 (0.11 g, 0.4 mmol) were added thereto. Sodium hydride (60% oil-based) (0.34 g, 8.4 mmol) was slowly added thereto at room temperature, and the mixture was stirred at room temperature overnight. Then, dilute hydrochloric acid was added thereto, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was dissolved in ethanol (10 mL), and an aqueous solution obtained by dissolving potassium hydroxide (1.40 g, 25 mmol) in water (5 mL) was added thereto at room temperature, and then the mixture was stirred at 80C for 3 hours. Water was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Tert-butyl methyl ether was added to the concentrate, and the aqueous layer was fractionated. Dilute hydrochloric acid was added to the resulting aqueous layer, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 0.59 g of 5-(1-fluoro-2-naphthylmethoxymethyl)isoxazole-3-carboxylic acid represented by the following formula. The product was subjected to a next reaction without purification., 123770-62-7

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Reference£º
Patent; Sumitomo Chemical Company, Limited; MITSUDERA, Hiromasa; AWASAGUCHI, Kenichiro; AWANO, Tomotsugu; UJIHARA, Kazuya; EP2952096; (2015); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Some tips on 123770-62-7

123770-62-7 Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate 8027233, aIsoxazoles compound, is more and more widely used in various fields.

EXAMPLE 7 (COMPOUND 20)3-Methylcarbamoylisoxazol-5-ylmethyl 2-[1-(6-chloroquinolin-2-yl)piperidin-4-yl]ethylcarbamate7.1. Ethyl 5-{2-[1-(6-chloroquinolin-2-yl)piperidin-4-yl-ethylcarbamoyloxymethyl}isoxazole-3-carboxylateThe process is performed according to the procedure described in Example 1 (step 1.7.). Starting with 0.5 g (1.1 mmol) of 4-nitrophenyl 2-[1-(6-chloroquinolin-2-yl)piperidin-4-yl]-ethylcarbamate, described in Example 6 (step 6.4.), 0.311 g (2.2 mmol) of N,N-diisopropylethylamine, 0.067 g (0.55 mmol) of N,N-dimethylaminopyridine and 0.188 g (1.1 mmol) of ethyl 5-hydroxymethylisoxazole-3-carboxylate, and after chromatography on silica gel, eluting with a 98/2 mixture of dichloromethane and methanol, 0.4 g of pure product is obtained in the form of a white powder.m.p. ( C.): 113-115 C.1H NMR (CDCl3) delta (ppm): 7.70 (d, 1H); 7.50 (m, 1H); 7.45 (m, 1H); 7.35 (m, 1H); 6.90 (d, 1H); 6.65 (s, 1H); 5.20 (s, 2H); 4.70 (m, 2H); 4.50-4.30 (m, 5H); 3.20 (m, 2H); 2.90 (broad t, 2H); 1.80 (broad d, 2H); 1.60-1.20 (m, 6H)., 123770-62-7

123770-62-7 Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate 8027233, aIsoxazoles compound, is more and more widely used in various fields.

Reference£º
Patent; SANOFI-AVENTIS; US2012/15950; (2012); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

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The synthetic route of 123770-62-7 has been constantly updated, and we look forward to future research findings.

123770-62-7, A solution of sodium hydroxide in water (2M; 50 mL) was added to a mixture of ethyl 5- (hydroxymethyl)isoxazole-3-carboxylate (8.67 g; 50.66 mmol) in ethanol (30 mL) and stirred vigorously for 2 hours. The solution was concentrated under reduced pressure,diluted in water and extracted with dichloromethane. The aqueous layer was acidified to pH 1 with hydrochloric acid 6N and extracted several times with ethyl acetate. The organic layer was dried and concentrated under reduced pressure to yield 5.43 g (75%) of 5-(hydroxymethyl)isoxazole-3-carboxylic acid as a white solid.

The synthetic route of 123770-62-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; REMYND N.V.; GRIFFIOEN, Johan, Gerard; PRINCEN, Katrien; VAN DOOREN, Tom, Francois, L.; DE WITTE, Koen; (189 pag.)WO2018/206757; (2018); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Some tips on 123770-62-7

123770-62-7 Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate 8027233, aIsoxazoles compound, is more and more widely used in various.

Reference Production Example 87 (0729) 60% Sodium hydride (1.40 g, 35.08 mmol) was added to dehydrated N,N-dimethylformamide (20 ml) cooled to 0C, under a nitrogen atmosphere, and a dehydrated N,N-dimethylformamide (10 ml) solution of ethyl 5-hydroxymethylisoxazole-3-carboxylate (4.0 g, 23.39 mmol) was added dropwise thereto over 10 minutes, and then the mixture was further stirred for 30 minutes. A dehydrated N,N-dimethylformamide (10 m) solution of 2-bromomethyl-5-chlorothiophene (3.9 g, 23.39 mmol) was added thereto, and the mixture was heated to room temperature and stirred for 16 hours. The reaction mixture was added to a saturated aqueous ammonium chloride solution, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 2.6 g of ethyl 5-(5-chlorothiophen-2-ylmethyl)oxymethylisoxazole-3-carboxy late represented by the following formula. 1H-NMR (CDCl3, TMS, delta (ppm)) : 6.80 (m, 2H), 6.68(s, 1H), 4.65 (s, 4H), 4.43 (q, 2H), 1.42 (t, 3H), 123770-62-7

123770-62-7 Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate 8027233, aIsoxazoles compound, is more and more widely used in various.

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123770-62-7 Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate 8027233, aIsoxazoles compound, is more and more widely used in various.

123770-62-7, Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reference Production Example 99 (0741) Ethyl 5-hydroxymethylisoxazole-3-carboxylate (1.71 g, 10.0 mmol), 2,2,2-trifluoroethylmethanesulfonate (5.34 g, 30 mmol), N,N-dimethylformamide (30 ml) and 60% sodium hydride (0.48 g, 12.0 mmol) were mixed at 0C, under a nitrogen atmosphere. The mixture was heated to room temperature and stirred for 16 hours, then added to a saturated aqueous ammonium chloride solution, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with water and saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was applied to a silica gel column chromatography to obtain 1.02 g of ethyl 5-(2,2,2-trifluoroethoxymethyl)isoxazole-3-carboxylate represented by the following formula. 1H-NMR (CDCl3, TMS, delta (ppm)) : 1.41 (3H, t), 3.91(2H, q), 4.43(2H, q), 4.80(2H, s), 6.73(1H, s), 123770-62-7

123770-62-7 Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate 8027233, aIsoxazoles compound, is more and more widely used in various.

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Ethyl chlorooximidoacetate (10 g, 66 mmol) in CHCl3 (80 mL) is slowly added to propargyl alcohol (4.7 mL, 81 mmol) and K2CO3 (27 g, 198 mmol) in CHCl3 (80 mL). The addition is accompanied by an exothermic reaction which causes the chloroform to reflux. After being allowed to cool to RT, the mixture is stirred overnight. The reaction mixture is filtered and the residue is rinsed with chloroform and concentrated in vacuo. The crude product is purified by chromatohraphy (Biotage 40M, EtOAc/Hex:20/80) to yield 3.23 g (29% yield) of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate as an oil. 1H NMR (400 MHz, CDCl3) delta 6.69, 4.86, 4.45, 4.42. A solution of diethylaminosulfur trifluoride (DAST) (2.8 mL, 21 mmol) in 30 mL CH2Cl2 is added dropwise to a solution of ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate (3.0 g, 18 mmol) in 30 mL CH2Cl2 at -78 C. The mixture is stirred at -78 C. for 1 h and then warmed to RT over 3 h. Water (10 mL) and 30 mL of 2.5% aqueous sodium bicarbonate solution are added successively and the organic layer is separated, dried (MgSO4) and evaporated in vacuo. The residue is purified by chromatography (Biotage 40M, EtOAc/Hex:20/80) to give 1.83 g (60% yield) of ethyl 5-(fluoromethyl)isoxazole-3-carboxylate as an oil. 1H NMR (400 MHz, CDCl3) delta 6.82, 5.54, 5.42, 4.47, 1.43. 10% Aqueous sodium hydroxide solution (5 mL) is added to a solution of ethyl 5-(fluoromethyl)isoxazole-3-carboxylate (1.82 g, 10 mmol) in ethanol (30 mL) at RT. The mixture is stirred for 2 h and the solvents are evaporated in vacuo. The residue is dissolved in water and acidified to pH 1 with 35% HCl. Ethanol is added, solvents are evaporated in vacuo and the residue is azeotroped with ethanol. Ethanol is added and the mixture filtered to remove inorganic solids. Evaporation in vacuo of the filtrate gives 0.95 g (63% yield) of 5-(fluoromethyl)isoxazole-3-carboxylic acid as a tan solid. 1H NMR (400 MHz, DMSO-d6) delta 7.05, 5.67, 5.56. Oxalyl chloride (0.85 mL, 9.8 mmol) is added dropwise to a suspension of 5-(fluoromethyl)isoxazole-3-carboxylic acid (0.94 g, 6.5 mmol) and a catalytic amount of DMF in 20 mL CH2Cl2. After 1 h, the volatiles are removed in vacuo and the remaining residue is dissolved in acetone. To this solution is added an aqueous solution of sodium azide (0.59 g, 9.1 mmol) at 0 C. with vigorous stirring. Volatiles are removed in vacuo and the residue washed with water and dried under nitrogen to yield 0.57 g (51% yield) of 5-(fluoromethyl)isoxazole-3-carbonyl azide as a white solid. 1H NMR (400 MHz, DMSO-d6) delta 7.21, 5.71, 5.59. Example 605 is prepared according to Method F, making non-critical modifications. Yield 37%. HRMS (ESI) calcd for Cl3H13ClFN3O4+H 330.0657 found 330.0649

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Reference£º
Patent; Piotrowski, David W.; Rogers, Bruce N.; McWhorter JR., William W.; Walker, Daniel Patrick; Corbett, Jeffrey W.; Groppi JR., Vincent E.; Rudmann, Daniel G.; US2003/236287; (2003); A1;,
Isoxazole – Wikipedia
Isoxazole | C3H3NO – PubChem

Simple exploration of 123770-62-7

123770-62-7 Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate 8027233, aIsoxazoles compound, is more and more widely used in various.

123770-62-7, Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate is a Isoxazoles compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Reference Production Example 199 (0842) Ethyl 5-hydroxymethylisoxazole-3-carboxylate (0.29 g, 1.7 mmol) was dissolved in tetrahydrofuran (10 mL), and 3-fluoro-2-naphthylmethyl bromide (0.48 g, 2.0 mmol) and 18-crown-6 (0.05 g, 0.2 mmol) were added thereto. Sodium hydride (60% oil-based) (0.14 g, 3.4 mmol) was slowly added thereto at room temperature, and the mixture was stirred at room temperature overnight. Then, dilute hydrochloric acid was added thereto, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was dissolved in ethanol (4 mL), and an aqueous solution obtained by dissolving potassium hydroxide (0.56 g, 10 mmol) in water (2 mL) was added thereto at room temperature, and then the mixture was stirred at 80C for 3 hours. Water was added to the reaction mixture, and the mixture was concentrated under reduced pressure. Tert-butyl methyl ether was added to the concentrate, and the aqueous layer was fractionated. Dilute hydrochloric acid was added to the resulting aqueous layer, and the mixture was extracted three times with ethyl acetate. The organic layer was washed with saturated saline water, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 0.48 g of 5-(3-fluoro-2-naphthylmethoxymethyl)isoxazole-3-carboxylic acid represented by the following formula. The product was subjected to a next reaction without purification

123770-62-7 Ethyl 5-(hydroxymethyl)isoxazole-3-carboxylate 8027233, aIsoxazoles compound, is more and more widely used in various.