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CAS No. : | 4136-95-2 | MDL No. : | MFCD00075323 |
Formula : | C7H2Cl4O | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | OZGSEIVTQLXWRO-UHFFFAOYSA-N |
M.W : | 243.90 | Pubchem ID : | 2733703 |
Synonyms : |
|
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P280-P305+P351+P338-P310 | UN#: | 3265 |
Hazard Statements: | H314 | Packing Group: | Ⅱ |
GHS Pictogram: |
* 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 thionyl chloride;Reflux; | A solution of <strong>[50-43-1]2,4,6-trichlorobenzoic acid</strong> (337 mg, 1.5 mmol) in SOCl2 (10 ml) was heated at reflux overnight and then cooled to room temperature. The reaction was concentrated under reduced pressure and to afford the desired acid chloride intermediate in quantitative yield. This material was used in the following step without purification | |
With thionyl chloride; at 70℃; for 2h; | Step 1 )A solution of commercially available compound 1 (448 mg, 2 mmol) in SOC (5 mL) was stirred at 70 C for 2 h, followed by concentration under reduced pressure to afford compound 2 as the crude product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; at 0℃; for 2h; | General procedure: To a cooled (0 °C) solution of S12a (105.7 mg, 0.240 mmol) in THF (10 mL) were added 2,4,6-trichlorobenzoyl chloride (56.2 muL, 0.360 mmol) and Et3N (58.5 muL, 0.420 mmol). After stirring for 2 h at 0 °C, S8 (100.3 mg, 0.120 mmol) in THF (4 mL) and DMAP (29.3 mg, 0.240 mmol) were added at 0 °C. After stirring for 1 h at 25 °C, the reaction was quenched by the addition of saturated NH4Cl solution and diluted with EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, EtOAc/hexanes = 1/1) to afford S13a (146.4 mg, 91percent) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0℃; for 1h; | To a solution of <strong>[96402-49-2]Fmoc-L-1-naphthylalanine</strong> (0.052 g, 0.119 mmol, 1.95 equiv) in THF (1 mL) at 0 °C were added Hunig's base (0.028 g, 0.219 mmol, 3.59 equiv) and 2,4,6-trichlorobenzoyl chloride (0.031 g, 0.128 mmol, 2.09 equiv). The reaction mixture was stirred at 0 °C for 1 h, when TLC indicated the formation of the anhydride. The alcohol 13 (0.041 g, 0.061 mmol, 1 equiv) and DMAP (0.009 g, 0.074 mmol, 1.2 equiv) in THF (1 mL) were added to the reaction mixture at 0 °C. It was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo and flash chromatography purification on silica gel in ethyl acetate/hexanes (20-60percent) yielded the acyclic precursor 14c (0.065 g, 98; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With dmap; In dichloromethane; at 0 - 20℃;Inert atmosphere; | General procedure: Acyl chloride (0.18 mmol, 1.1 eq) was added at 0 C to a solution of <strong>[436-77-1]fangchinoline</strong> (100 mg, 0.16 mmol) and DMAP (0.032 mmol, 0.2eq) in 2 mL dry CH2Cl2 under argon and stirred for 2-4 h. The reaction mixture was quenched with a saturated aqueous solution of sodium bicarbonate and extracted three times with CH2Cl2. The combined organic phase was dried over anhydrous magnesium sulfate before vacuum suction filtration. The removal of the solventin vacuo afforded the crude product, which was chromatographied on silica gel (CH2Cl2/MeOH, 50/1 v/v, 0.1% TEA) to provide the pureproduct 1a-1e, 2a-2g, 3a-3e and 4a-4h. |
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