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Chemical Structure| 407-62-5 Chemical Structure| 407-62-5

Structure of 407-62-5

Chemical Structure| 407-62-5

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Product Details of [ 407-62-5 ]

CAS No. :407-62-5
Formula : C5H7F3O2
M.W : 156.10
SMILES Code : O=C(O)CCCC(F)(F)F
MDL No. :MFCD02262192
InChI Key :RUEXKRNFAABHHU-UHFFFAOYSA-N
Pubchem ID :2782446

Safety of [ 407-62-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H302-H312-H314-H332
Precautionary Statements:P260-P261-P264-P270-P271-P280-P301+P312-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P312-P321-P322-P330-P363-P405-P501
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 407-62-5 ]

* 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 [ 407-62-5 ]

[ 407-62-5 ] Synthesis Path-Downstream   1~2

  • 2
  • [ 407-62-5 ]
  • [ 17016-83-0 ]
  • [ 1401067-00-2 ]
YieldReaction ConditionsOperation in experiment
86% Intermediate S-1H: (4S)-4-(Propan-2-yl)-3-(5,5,5-trifluoropentanoyl)-1,3-oxazolidin-2-one [0285] 5,5,5-trifluoropentanoic acid (5.04 g, 32.3 mmol) in DCM (50 mL) and DMF (3 drops) was added oxalyl chloride (3.4 mL, 38.8 mmol) dropwise over 5 min. The solution was stirred until all bubbling subsided. The reaction mixture was concentrated under reduced pressure to give pale yellow oil. To a separate flask charged with a solution of (4S)-4-(propan-2-yl)-1,3-oxazolidin-2-one (4.18 g, 32.4 mmol) in THF (100 mL) at -78 C. was added n-BuLi (2.5M in hexane) (13.0 mL, 32.5 mmol) dropwise via syringe over 5 min. After stirring for 10 min, the above acid chloride, dissolved in THF (20 mL), was added via cannula over 15 min. The reaction mixture was warmed to 0 C., and was allowed to warm to room temperature as the bath warmed and stirred overnight. To the reaction mixture was added saturated NH4Cl, and the mixture was extracted with EtOAc (2×). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography (Teledyne ISCO CombiFlash Rf, 5% to 60% solvent A/B=hexanes/EtOAc, REDISEP SiO2 120 g). Concentration of the appropriate fractions provided Intermediate S-1H (7.39 g, 86%) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ ppm 4.44 (1H, dt, J=8.31, 3.53Hz), 4.30 (1H, t, J=8.69 Hz), 4.23 (1H, dd, J=9.06, 3.02Hz), 2.98-3.08 (2H, m), 2.32-2.44 (1H, m, J=13.91, 7.02, 7.02, 4.03Hz), 2.13-2.25 (2H, m), 1.88-2.00 (2H, m), 0.93 (3H, d, J=7.05 Hz), 0.88 (3H, d, J=6.80 Hz).
86% To a stirred solution of 5,5,5-trifluoropentanoic acid (5.04 g, 32.3 mmol) inDCM (50 mL) and DMF (3 drops) was added oxalyl chloride (3.4 mL, 38.8 mmol)dropwise over 5 min and the solution was stirred until all bubbling subsided. Thereaction mixture was concentrated under reduced pressure to give pale yellow oil. To aseparate flask charged with a solution of ( 48)-4-(propan-2-yl)-I ,3-oxazolidin-2-one ( 4.I820 g, 32.4 mmol) in THF (IOO mL) at -78 oc was added n-BuLi (2.5M in hexane, 13.0 mL,32.5 mmol) dropwise via syringe over 5 min. After stirring for IO min, the above acidchloride dissolved in THF (20 mL) was added via cannula over I5 min. The reactionmixture was warmed to 0 C, and was allowed to warm to room temperature as the bathwarmed and stirred overnight. To the reaction mixture was added saturated NH4Cl, and25 then extracted with EtOAc (2x). The combined organics were washed with brine, dried(Na2S04), filtered and concentrated under reduced pressure. The crude material waspurified by flash chromatography (Teledyne ISCO CombiFlash Rf, 5% to 60% solventA/B=hexanes/EtOAc, REDISEP Si02 I20g). Concentration of appropriate fractionsprovided Intermediate S-IB (7.39 g, 86%) as a colorless oil: 1H NMR (400 MHz, CDCh) 8 ppm 4.44 (I H, dt, J=8.3I, 3.53 Hz), 4.30 (I H, t, J=8.69 Hz), 4.23 (I H, dd, J=9.06,3.02 Hz), 2.98-3.08 (2 H, m), 2.32-2.44 (I H, m, J=13.9I, 7.02, 7.02, 4.03 Hz), 2.13-2.25(2 H, m), 1.88-2.00 (2 H, m), 0.93 (3 H, d, J=7.05 Hz), 0.88 (3 H, d, J=6.80 Hz).
86% [00141] To a stirred solution of 5,5,5-trifluoropentanoic acid (5.04 g, 32.3 mmol) inDCM (50 mL) and DMF (3 drops) was added oxalyl chloride (3.4 mL, 38.8 mmol)dropwise over 5 min. The solution was stirred until all bubbling subsided. The reactionmixture was concentrated under reduced pressure to give a pale yellow oil. To a separateflask, charged with a solution of ( 48)-4-(propan-2-yl)-1 ,3-oxazolidin-2-one ( 4.18 g, 32.420 mmol) in THF (100 mL) at -78 oc was added n-BuLi (13.0 mL, 32.5 mmol, 2.5M inhexane) dropwise via syringe over 5 min. After stirring for 1 0 min, the above acidchloride, dissolved in THF (20 mL ), was added via cannula over 15 min. The reactionmixture was warmed to 0 oc and was allowed to warm to room temperature as the bathwarmed and stirred overnight. To the reaction mixture was then added saturated NH4Cl,25 and it was then extracted with EtOAc (2x). The combined organics were washed withbrine, dried (Na2S04), filtered and concentrated under reduced pressure. The crudematerial was purified by silica gel chromatography (hexanes/EtOAc) to provideIntermediate S-1G (7.39 g, 86%) as a colorless oil: 1H NMR (400 MHz, CDCh) 8 4.44 (1H, dt, J=8.31, 3.53 Hz), 4.30 (1 H, t, J=8.69 Hz), 4.23 (1 H, dd, J=9.06, 3.02 Hz), 2.98-3.08 (2 H, m), 2.32-2.44 (1 H, m, J=13.91, 7.02, 7.02, 4.03 Hz), 2.13-2.25 (2 H, m), 1.88-2.00 (2 H, m), 0.93 (3 H, d, J=7.05 Hz), 0.88 (3 H, d, J=6.80 Hz).
86% Preparation A-i B: (4S)-4-(Propan-2-yl)-3 -(5,5,5 -trifluoropentanoyl)- 1,3 -oxazolidin-2- one [00143j To a stirred solution of 5,5,5-trifluoropentanoic acid (5.04 g, 32.3 mmol) in DCM (50 mL) and DMF (3 drops) was added oxalyl chloride (3.4 mL, 38.8 mmol) dropwise over 5 mm and the solution was stirred until all bubbling subsided. The reaction mixture was concentrated under reduced pressure to give pale yellow oil. To a separate flask charged with a solution of (4S)-4-(propan-2-yl)- 1 ,3-oxazolidin-2-one (4.18g, 32.4 mmol) in THF (100 mL) at -78 C was added n-BuLi (2.5M in hexane) (13.0 mL,32.5 mmol) dropwise via syringe over 5 mm. After stirring for 10 mm, the above acid chloride dissolved in THF (20 mL) was added via cannula over 15 mm. The reaction mixture was warmed to 0 C, and was allowed to warm to room temperature as the bath warmed and stirred overnight. To the reaction mixture was added saturated NH4C1, andthe mixture was then extracted with EtOAc (2x). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography (Teledyne ISCO CombiFlash Rf, 5% to 60% solvent A/B=hexanes/EtOAc, REDISEP Si02 120g). Concentration of appropriate fractions provided Preparation A-lB (7.39 g, 86%) as a colorless oil: ‘HNMR (400 MHz, CDC13) ö ppm 4.44 (1 H, dt, J8.31, 3.53 Hz), 4.30 (1 H, t, J8.69 Hz),4.23 (1 H, dd, J=9.06, 3.02 Hz), 2.98-3.08 (2 H, m), 2.32-2.44 (1 H, m, J=13.91, 7.02,7.02, 4.03 Hz), 2.13-2.25 (2 H, m), 1.88-2.00 (2 H, m), 0.93 (3 H, d, J=7.05 Hz), 0.88 (3 H, d, J=6.80 Hz).
86% Intermediate S-i H: (4S)-4-(Propan-2-yl)-3 -(5,5,5 -trifluoropentanoyl)- 1,3 -oxazolidin-2- one[00146j To a stirred solution of 5,5,5-trifluoropentanoic acid (5.04 g, 32.3 mmol) in DCM (50 mL) and DMF (3 drops) was added oxalyl chloride (3.4 mL, 38.8 mmol) dropwise over 5 mm and the solution was stirred until all bubbling subsided. The reaction mixture was concentrated under reduced pressure to give pale yellow oil. To a separate flask charged with a solution of (4S)-4-(propan-2-yl)- 1 ,3-oxazolidin-2-one (4.18g, 32.4 mmol) in THF (100 mL) at -78 C was added n-BuLi (2.5M in hexane) (13.0 mL,32.5 mmol) dropwise via syringe over 5 mm. After stirring for 10 mm, the above acid chloride dissolved in THF (20 mL) was added via cannula over 15 mm. The reaction mixture was warmed to 0 C, and was allowed to warm to room temperature as the bath warmed and stirred overnight. To the reaction mixture was added saturated NH4C1, andthen extracted with EtOAc (2x). The combined organics were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography (Teledyne ISCO CombiFlash Rf, 5% to 60% solvent A/B=hexanes/EtOAc, REDISEP Si02 1 20g). Concentration of appropriate fractions provided Intermediate S-1H (7.39 g, 86%) as a colorless oil: ‘H NMR (400 MHz, CDC13)o ppm 4.44 (1 H, dt, J=8.31, 3.53 Hz), 4.30 (1 H, t, J=8.69 Hz), 4.23 (1 H, dd, J9.06,3.02 Hz), 2.98-3.08 (2 H, m), 2.32-2.44 (1 H, m, J=13.91, 7.02, 7.02, 4.03 Hz), 2.13-2.25(2 H, m), 1.88-2.00 (2 H, m), 0.93 (3 H, d, J=7.05 Hz), 0.88 (3 H, d, J6.80 Hz).
86% To a stirred solution of 5,5,5-trifluoropentanoic acid (5.04 g, 32.3 mmol) inDCM (50 mL) and DMF (3 drops) was added oxalyl chloride (3.4 mL, 38.8 mmol)dropwise over 5 min. The solution was stirred until all bubbling subsided. The reaction5 mixture was concentrated under reduced pressure to give a pale yellow oil. To a separateflask charged with a solution of ( 48)-4-(propan-2-yl)-1 ,3-oxazolidin-2-one ( 4.18 g, 32.4mmol) in THF (100 mL) at -78 oc was added n-BuLi (13.0 mL, 32.5 mmol, 2.5M inhexane) dropwise via syringe over 5 min. After stirring for 1 0 min, the above acidchloride dissolved in THF (20 mL) was added via cannula over 15 min. The reaction10 mixture was warmed to 0 C, and was allowed to warm to room temperature as the bathwarmed and stirred overnight. To the reaction mixture was added saturated NH4Cl, andthen extracted with EtOAc (2x). The combined organics were washed with brine, dried(Na2S04), filtered and concentrated under reduced pressure. The crude material waspurified by silica gel chromatography (hexanes/EtOAc) to provide Intermediate S IA15 (7.39 g, 86%) as a colorless oil: 1H NMR (400 MHz, CDCh) 8 4.44 (1 H, dt, J=8.31, 3.53Hz), 4.30 (1 H, t, J=8.69 Hz), 4.23 (1 H, dd, J=9.06, 3.02 Hz), 2.98-3.08 (2 H, m), 2.32-2.44 (1 H, m, J=13.91, 7.02, 7.02, 4.03 Hz), 2.13-2.25 (2 H, m), 1.88-2.00 (2 H, m), 0.93(3 H, d, J=7.05 Hz), 0.88 (3 H, d, J=6.80 Hz).

 

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