Structure of 57330-59-3
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 57330-59-3 |
Formula : | C10H8F3NO4 |
M.W : | 263.17 |
SMILES Code : | CC(CC1=CC=C(OC(F)(F)F)C=C1[N+]([O-])=O)=O |
MDL No. : | MFCD17015785 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nitrous acid isobutyl ester;copper dichloride; at 18 - 50℃; for 1 - 2h;Product distribution / selectivity; | Step 3; Meerwein arylationlsopropenyl acetate CuCI2, i-butylnitrite A vessel was charged with isopropenyl acetate (30 L) followed by copper(II)chloride (2.93 Kg) in one portion at 18-25 0C with stirring. The temperature of the solution was adjusted to 40-45 0C. A solution of aniline 4 (4.05 Kg) in isopropenyl acetate (5 L) was added to the reaction mixture via an addition funnel over 1-2 h concomitantly with the addition of isobutyl nitrite (2.84 L) in a separate addition funnel over the same amount of time by keeping the reaction temperature at 40-50 0C.The reaction mixture was cooled to 18-22 0C, diluted with toluene (21.5 L) and quenched by addition of 1.0 N HCl (21.5 L). The reaction mixture was stirred for 15 min. The organic layer was washed with water (21.5 L)5 NaHCO3 aq sat (21.5 L) and water (2.5 L). The organic layer was concentrated under partial vacuum (max temp 20 0C) and the solvent switched to toluene. The volume was adjusted to 10.75 L and the homogeneous amber solution is cooled to 5 to -10 0C. Heptane (3.6 L) was added and the mixture aged for Ih. Heptane (37 L) was slowly added keeping the temperature at -5 to -10 0C. The slurry was cooled to -25 to -20 0C, aged 1 h at -25 to -20 0C and filtered.. The dark yellow cake was washed with toluene/heptane (1:6 v/v, 1 IL ) at -25 to -20 0C, and heptane (4 L) at -25 to -20 0C and dried at ambient temperature under partial vacuum with a flow of nitrogen to afford the ketone 5.; EXAMPLE 9; The conversion of Compound 4 of the synthetic procedure in Example 1 to Compound 6 can also be carried out by the following procedure: Meerwein Reaction and Ketalization; A solution of nitroaniline 4 (22.2Ig) in isopropenyl acetate (22mL) and a solution of iBuONO (94%, 13.7Ig) are each added from separate addition funnels at ca the same rate (+/- 10%) over Ih to a suspension of CuC12 (2.0Ig) in 20OmL isopropenyl acetate maintained at 40-50 C. The mixture is aged for Ih at 40-50 0C and cooled to 25 C. Toluene (10OmL) is added and the mixture is washed with IM HCl (2x15mL); most of the copper is concentrated in these two small aq. washes) and then with water (2x10OmL). The organic phase is concentrated to 50 mL and at constant volume solvent switched to toluene using 10OmL toluene at 200 Torr. The mixture is then constant volume solvent switched to EtOH using 15OmL EtOH at 200 Torr. The solution containing nitroketone 5 in 5OmL EtOH was mixed with EPO <DP n="24"/>ethylene glycol (9.3 Ig), (EtO)3CH (21.03 g), and p-TsOH (0.5Og), and the solution was heated to 45 C for 16h or 80 0C for l-2h and was then cooled to 25C. Conversion of the nitroketone 5 was monitored by HPLC. |
Tags: 57330-59-3 synthesis path| 57330-59-3 SDS| 57330-59-3 COA| 57330-59-3 purity| 57330-59-3 application| 57330-59-3 NMR| 57330-59-3 COA| 57330-59-3 structure
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