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Chemical Structure| 1103500-32-8 Chemical Structure| 1103500-32-8

Structure of 1103500-32-8

Chemical Structure| 1103500-32-8

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Product Details of [ 1103500-32-8 ]

CAS No. :1103500-32-8
Formula : C15H12F3NO4
M.W : 327.26
SMILES Code : O=C(C1=C(C2CC2)ON=C1C3=CC=CC=C3OC(F)(F)F)OC
MDL No. :MFCD22370412

Safety of [ 1103500-32-8 ]

Application In Synthesis of [ 1103500-32-8 ]

* 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 [ 1103500-32-8 ]

[ 1103500-32-8 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 1383740-01-9 ]
  • [ 32249-35-7 ]
  • [ 1103500-32-8 ]
YieldReaction ConditionsOperation in experiment
55% With triethylamine; at -5℃; Methyl 3-cyclopropyl-3-oxopropanoate (189.87 g, 1.34 mol) was added to compound ( T4-c) (160 g, 667.84 mmol), the reaction was stirred at -5C, triethylamine (500 mL) was added dropwise, and the reaction was performed at -5C overnight. The reaction solution was poured into water (20 L), and mechanically stirred for 30 minutes, to result in a solid. A yellow solid was obtained by suction filtration, and dried at 50C overnight, to afford compound (T4-d) (120 g, yield: 55%).
With potassium carbonate; In tetrahydrofuran; at -10 - 35℃; for 6h; Potassium carbonate (11 g, 79.7 mmol, 1.09 equiv) was suspended in THF (100 mL) and the mixture was stirred. A solution of <strong>[32249-35-7]methyl 3-cyclopropyl-3-oxopropanoate</strong> (11 g, 77.5 mmol, 1.06 equiv) in 50ml THF was added to the above stirred mixture and stirred for 30 min at -10 C. To this reaction mixture was added a solution of (Z)-2-(trifluoromethoxy)benzoyl chloride oxime (17.6 g, 73.3 mmol, 1.00 equiv) in THF (50 mL) at -5 C and then allowed to stir for 6 h at 35 C . The reaction mixture was diluted with 200 mL of H20, extracted with ethyl acetate (2 x 300 mL). The organic layer was washed with brine (2 x 200 mL), dried over anhydrous sodium sulfate, concentrated under vacuum, and then purified by silica gel columnchromatography using ethyl acetate/petroleum ether (1: 100-1:20) eluent to afford methyl 5- cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazole-4-carboxylate as a white solid.
Potassium carbonate (11.0 g, 79.7 mmol, 1.09 equiv) was suspended in THF (100 mL). Then the solution of <strong>[32249-35-7]methyl 3-cyclopropyl-3-oxopropanoate</strong> (11.0 g, 77.5 mmol, 1.06 equiv) in 50ml THF was added to the above stirred mixture at -10 C. The resulting solution was stirred for 30 min at -10 C. To this was added a solution of (Z)-2-(trifluoromethoxy)benzoyl chloride oxime (17.6 g, 73.3 mmol, 1.00 equiv) in THF (50 mL) at -5C. The resulting solution was allowed to stir for 6 hours at 35C. The resulting solution was diluted with 200 mL of H20, extracted with 2 x 300 mL of ethyl acetate. The organic layer was washed with 2 x 200 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum, then purified by silica gel column with ethyl acetate/petroleum ether (1:100-1:20), which gave methyl 5- cyclopropyl-3-(2-(trifluoromethoxy)phenyl)isoxazole-4-carboxylate as a white solid.
With potassium carbonate; In tetrahydrofuran; at -5 - 35℃; for 6h; Potassium carbonate (11.0 g, 79.7 mmol, 1.09 equiv) was suspended in THF (100 mL). Then the solution of <strong>[32249-35-7]methyl 3-cyclopropyl-3-oxopropanoate</strong> (11.0 g, 77.5 mmol, 1.06 equiv) in 50ml THF was added to the above stirred mixture at -10 C. The resulting solution was stirred for 30 min at -10 C. To this was added a solution of (Z)-2-(trifluoromethoxy)benzoyl chloride oxime (17.6 g, 73.3 mmol, 1.00 equiv) in THF (50 mL) at -5C. The resulting solution was allowed to stir for 6 hours at 35C. The resulting solution was diluted with 200 mL of H20, extracted with 2 x 300 mL of ethyl acetate. The organic layer was washed with 2 x 200 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum, then purified by silica gel column with ethyl acetate/petroleum ether (1: 100-1:20). Methyl 5-cyclopropyl-3-(2- (trifluoromethoxy)phenyl)isoxazole-4-carboxylate was obtained as a white solid.
Potassium carbonate (11 g, 79.7 mmol, 1.09 equiv) was suspended in THF (100 mL) and the mixture was stirred. A solution of <strong>[32249-35-7]methyl 3-cyclopropyl-3-oxopropanoate</strong> (11 g, 77.5 mmol, 1.06 equiv) in 50 ml THF was added to the above stirred mixture and stirred for 30 min at -10C. To this reaction mixture was added a solution of (Z)-2-(trifluoromethoxy)benzoyl chloride oxime (17.6 g, 73.3 mmol, 1.00 equiv) in THF (50 mL) at -5C. and then allowed to stir for 6 h at 35C. The reaction mixture was diluted with 200 mL of H2O, extracted with ethyl acetate (2 x 300 mL). The organic layer was washed with brine (2 x 200 mL), dried over anhydrous sodium sulfate, concentrated under vacuum, and then purified by silica gel column chromatography using ethyl acetate/petroleum ether (1 : 100-1 :20) eluent to afford methyl 5-cyclopropyl-3-(2- (trifluoromethoxy)phenyl)isoxazole-4-carboxylate as a white solid.
120 g With triethylamine; In dimethyl sulfoxide; at -5 - 25℃; Methyl 3-cyclopropyl-3-oxopropionate compound (189.87g, 1.34mol) and triethylamine (500mL) were dissolved in DMSO (500mL), and the reaction was stirred at -5C,A solution of compound In-3 (160 g, 667.84 mmol) in DMSO (500 mL) was added dropwise,React overnight at 25C.Pour the reaction solution into water (20L),Stir mechanically for 30 minutes,Solids appear,Suction filtration to obtain a yellow solid,Dry overnight at 50C,The title compound In-4 (120 g) was obtained.

  • 2
  • [ 543713-03-7 ]
  • [ 32249-35-7 ]
  • [ 1103500-32-8 ]
YieldReaction ConditionsOperation in experiment
6. Preparation of methyl 5-cyclopropyl-3-(2-(trifluoromethoxy)phenyl) isoxazol-4-formate Potassium carbonate (10.44 g, 75.52 mmol) was added to THF(100 mL), and the solution of <strong>[32249-35-7]methyl 3-cyclopropyl-3-oxopropionate</strong> (10.44 g, 73.4 mmol) in THF (50 mL) was added to the reaction system. The system was stirred at -10 C for 30 mins. The solution of N-hydroxy-2-(trifluoromethoxy)benzimidoyl chloride (16.6 g, crude product) in THF (50 mL) was then added to the reaction system at -5 C, and the system reacted at 35 C for 6 hrs. The reaction solution was diluted with water (200 mL), and extracted with ethyl acetate (500 mL x 3). The organic phase was dried, concentrated, and purified by a silica-gel column (petroleum ether : ethyl acetate = 5:1) to obtain a product (11.3 g, yield: 47.1%).
2.5 g With sodium methylate; In methanol; at -10 - 35℃; for 12h; Sodium methoxide (2.6 g, 48.9 mmol) was suspended in CH3OH(50 mL), and the mixture was cooled to 10 C and treated with asolution of <strong>[32249-35-7]methyl 3-cyclopropyl-3-oxopropanoate</strong> (5.3 g,37.6 mmol) in CH3OH (20 mL) dropwise over 5 min. To above reactionmixture was then slowly added a solution of compound 3 (4.5 g, 18.8 mmol) in CH3OH at 10 C. The reactionwas warmed to35 C and stirred for 12 h. After completion, the reaction mixturewas diluted with water and extracted with ethyl acetate. Thecombined organic layer was washed with brine, dried over anhydroussodium sulfate, concentrated under vacuum, and then purifiedby silica gel column chromatography using ethyl acetate/petroleum ether to afford compound 4 as a white solid, 2.5 g in 41%yield; 1H NMR (DMSO-d6, 300 MHz) d 7.65e7.60 (m, 1H, Ph),7.53(dd, J 7.6, 2 Hz, 1H, Ph), 7.48e7.43 (m, 2H, Ph), 3.68 (s, 3H,eCOOCH3), 2.89 (m, J 6.8 Hz, 1H, eCH(CH2)2), 1.30 (m, J 6.8 Hz,4H, eCH(CH2)2); MS (ESI) m/z: 328.1 [MH].
2.5 g With sodium methylate; In methanol; at -5 - 35℃; for 12h;Cooling with ice; Under an ice-salt bath, NaOCH3 (2.64g, 48.9mmol) was dissolved in CH3OH to prepare solution B. Methyl 3-cyclopropyl-3-oxopropionate (5.34 g, 37.6 mmol) was dissolved in CH3OH. The solution B was slowly added to it, and the addition time was longer than 5 minutes. Dissolve 2-trifluoromethoxy-N-hydroxy-chlorobenzaldehyde oxime (4.5g, 18.8mmol) in CH3OH, add dropwise to the above mixture under an ice-salt bath, the reaction temperature should always be less than -5 . After 5 minutes, the ice salt bath was removed, the temperature was raised to 35C, and the reaction was carried out for 12 hours. The excess NaOCH3 was neutralized with CH3COOH, CH3OH was removed under reduced pressure, and extracted with EA and H2O. Dehydrate with saturated brine, dry with anhydrous Na2SO4, and spin dry. Purified by column chromatography, the product was 2.5 g, and the yield was 40.7%.
  • 3
  • [ 255820-47-4 ]
  • [ 32249-35-7 ]
  • [ 1103500-32-8 ]
YieldReaction ConditionsOperation in experiment
General procedure: 2-(Trifluoromethoxy)benzaidehyde was condensed with hydroxylamine hydrochloride in the presence of sodium hydroxide in ethanol to give the corresponding oxime. Oxidation of the oxime with Nchlorosuccinimide (NCS) gave a chloroxime, which was then immediately reacted with meth I 3-cyciopropyl-3 -oxopropanoate and potassium carbonate to form an isoxazole product Reduction of the methyl ester with lithium aluminum hydride in TI-IF afforded the corresponding alcohol. The alcohol wass then converted to the bromide with carbontetrabromide and triphenylphosphine. The bromide aikylated the hydroxy group of the endo isomer of N-BOG desmethyltropine with KOtBu, THE, and I -crown-6 ether. Removal of the N-BOC group with trifluoroacetic acid (TFA) gave the N-H tropane core (Scheme 1).
 

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