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CAS No. :149524-47-0 MDL No. :MFCD01013386
Formula : C14H12FNO2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 245.25 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 149524-47-0 ]

* 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.

  • Upstream synthesis route of [ 149524-47-0 ]
  • Downstream synthetic route of [ 149524-47-0 ]

[ 149524-47-0 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 60456-26-0 ]
  • [ 149524-47-0 ]
  • [ 149524-42-5 ]
YieldReaction ConditionsOperation in experiment
81%
Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1.33333 h; Inert atmosphere
Stage #2: at -78℃; for 1 h; Inert atmosphere
General procedure: Compound 2 (2 mmol) was dissolved in anhydrous THF (10 mL) then cooled to -78 C under nitrogen followed by slow addition of 1M LHMDS in THF solution (1.7 mL, 1.7 mmol) over 20 min. The resulting mixture was subsequently stirred at -78° C for 1 h before (R)-(-)-glycidyl butyrate (0.24 g, 1.7 mmol) was added drop wise at -78° C and the mixture was stirred at this temperature for 1 h then allowed to gradually warm to room temperature under stirring for 12 hrs. The reaction was quenched with DDW (10 mL) followed by EtOAc (4 mL). Then the two layers were separated and the aqueous layer was extracted with EtOAc (3×10 mL). The combined organic extracts were washed with saturated aqueous sodium chloride (3×5 mL), dried over Na2SO4, filtered, and concentrated under vacuum.  The crude product was then dissolved in DCM (10 mL) and allowed to stand overnight to get a white precipitate which was filtered and washed with DCM.
70%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667 h; Inert atmosphere
Stage #2: at -78 - 20℃; Inert atmosphere
To a solution of N-carbobenzyloxy-3-fluoroaniline 2 (132 g, 538 mmol) in THF (1.3 L) at -78 °C added slowly n-butyllithium 1.6 M in n-hexane (370 mL, 600 mmol) under nitrogen condition. After the solution was stirred at -78 °C for 10 min, (R)-(-)-glycidyl butylate (84.0 mL, 600 mmol) was slowly added. The mixture was stirred at -78 °C for 2 h and stirred at room temperature for 24 h. After completion of the reaction, an aqueous saturated ammonium chloride (NH4Cl) solution was added and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was recrystallized from EtOAc and n-hexane to give the title compound (80 g, 70percent). 1H NMR (DMSO-d6): δ 7.51 (d, J = 12.0 Hz, 1H), 7.40 (m, 1H), 7.34 (m, 1H), 6.93 (t, J = 6.8 Hz, 1H), 5.21 (t, J = 5.6 Hz, 1H), 4.70 (m, 1H), 4.07 (t, J = 9.2 Hz, 1H), 3.83 (m, 1H), 3.68 (m, 1H), 3.55 (m, 1H).
70%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 26 h;
Will be 132 gramsN-Benzyloxycarbonyl-3-fluoroaniline was dissolved1.3 liters of tetrahydrofuran,And the solution was cooled to -78 ° C.370 ml of n-butyllithium (1.6 mol / l, n-hexane) was slowly added to the solution under a nitrogen atmosphere and then stirred for 10 minutes.Will be 84 ml(R) - (-) - butyric acid glycidyl ester was slowly added to the reaction mixture,Glycidyl butyrateThe mixture was stirred at the same temperature for 2 hours and then allowed to react at room temperature for 24 hours. After completion of the reaction, an ammonium chloride solution was added to the solution and extracted with 0.5 liter of ethyl acetate at room temperature. The resulting organic layer was separated by brine and dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting residue was dissolved in 100 ml of ethyl acetate and washed with n-hexane to give a white crystal which was purified to 80 g of the title compound in 70percent yield.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 23, p. 5310 - 5321
[2] European Journal of Medicinal Chemistry, 2011, vol. 46, # 4, p. 1027 - 1039
[3] Patent: CN106146559, 2016, A, . Location in patent: Paragraph 0044; 0045
[4] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 9, p. 1009 - 1014
[5] Patent: US2010/234615, 2010, A1, . Location in patent: Page/Page column 36
[6] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5266 - 5269
[7] Patent: WO2016/77818, 2016, A1, . Location in patent: Paragraph 0210; 0212
[8] Patent: WO2017/200979, 2017, A1, . Location in patent: Paragraph 0195
  • 2
  • [ 121906-41-0 ]
  • [ 149524-47-0 ]
  • [ 149524-42-5 ]
YieldReaction ConditionsOperation in experiment
91.6%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 26 h; Inert atmosphere
To a solution of N-carbobenzyloxy-3-fluoroaniline 3 (39.00 g, 159 mmol) in anhydrous THF (200 mL) at −78 °C was slowly added n-butyllithium 2.5 M in n-hexane (71.3 mL, 178 mmol) under argon condition. After the solution was stirred at −78 °C for 10 min, (R)-(−)-glycidyl butylate (24.9 mL, 178 mmol) was slowly added. The mixture was stirred at −78°C for 2 h and stirred at room temperature for 24 h. After completion of the reaction, an aqueous saturated ammonium chloride solution (150 mL) was added and the mixture was extracted with ethyl acetate (200 mL × 2). The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was recrystallized from 20 percent ethyl acetate in petroleum ether to give the title compound (30.75 g, 91.6 percent). The 1H-NMR spectra were in accordance with the literature data.8) 1H-NMR (400 MHz, DMSO-d6) δ: 7.51–7.54 (m, 1H), 7.38–7.42 (m, 1H), 7.31–7.34 (m, 1H), 6.91–6.96 (m, 1H), 5.21 (t, 1H, J = 5.6 Hz), 4.68–4.73 (m, 1H), 4.08 (t, 1H, J = 9.2 Hz), 3.81–3.85 (m, 1H), 3.65–3.67 (m, 1H), 3.56–3.57 (m, 1H).
Reference: [1] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 2, p. 143 - 146
  • 3
  • [ 60456-26-0 ]
  • [ 149524-47-0 ]
  • [ 149524-42-5 ]
Reference: [1] Patent: US5565571, 1996, A,
  • 4
  • [ 149524-47-0 ]
  • [ 444335-16-4 ]
Reference: [1] Patent: CN106146559, 2016, A,
  • 5
  • [ 149524-47-0 ]
  • [ 856866-72-3 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2015, vol. 63, # 2, p. 143 - 146
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