Structure of 70987-78-9
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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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CAS No. : | 70987-78-9 |
Formula : | C10H12O4S |
M.W : | 228.26 |
SMILES Code : | O=S(OC[C@@H]1CO1)(C2=CC=C(C)C=C2)=O |
MDL No. : | MFCD00064489 |
InChI Key : | NOQXXYIGRPAZJC-VIFPVBQESA-N |
Pubchem ID : | 153296 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H317-H318-H341-H350-H411 |
Precautionary Statements: | P201-P273-P280-P305+P351+P338-P308+P313 |
Class: | 9 |
UN#: | 3077 |
Packing Group: | Ⅲ |
* 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 potassium carbonate; In N-methyl-acetamide; dichloromethane; water; Petroleum ether; | EXAMPLE 2 A stirred mixture of <strong>[18362-30-6]2-chloro-6-hydroxybenzaldehyde</strong> (4.4 g), (R)-glycidyl 4-toluenesulphonate (5.0 g) and potassium carbonate (3.9 g) in dimethylformamide (120 ml) was heated at 60° C. for 5 hours then allowed to stand at ambient temperature for 18 hours. The solvent was removed in vacuo, water (60 ml) was added and the mixture extracted with ether (3*100 ml). The combined extracts were dried over magnesium sulphate and the solvent evaporated. The residue was purified by flash chromatography on silica eluding with a 1:1 mixture of petroleum ether (b.p. 60-80° C.) and dichloromethane followed by a 19:1 mixture of dichloromethane and industrial methylated spirit. Appropriate fractions were combined and the solvent was removed in vacuo to give (R)-2-chloro-6-(2,3-epoxypropoxy)benzaldehyde (2.8 g) m.p. 62-64° C. | |
With potassium carbonate; In N-methyl-acetamide; dichloromethane; water; Petroleum ether; | EXAMPLE 9 A mixture of <strong>[18362-30-6]2-chloro-6-hydroxybenzaldehyde</strong> (4.4 g), (R)-glycidyl 4-toluenesulphonate (5.0 g) and potassium carbonate (3.9 g) in dimethylformamide (120 ml) was stirred and heated at 60° C. for 5 hours and allowed to cool over 18 hours. The solvent was removed in vacuo, water (60 ml) was added to the residue and the mixture extracted with ether (3*100 ml). The combined extracts were dried over magnesium sulphate and the solvent was evaporated. The residual oil was purified by flash chromatography on silica eluding with a 1:1 mixture of petroleum ether (b.p. 40-60° C.) and dichloromethane, followed by neat dichloromethane then a 19:1 mixture of dichloromethane and industrial methylated spirit. Appropriate fractions were combined and the solvent removed in vacuo to give (R)-2-chloro-6-(2,3-epoxypropoxy)benzaldehyde as a pale yellow solid (2.8 g). Other, incompletely purified, fractions gave material which was subjected to repeat chromatography, providing a second crop of product (0.5 g). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
l-[5-Benzyloxy-2-((R)-l-oxiranylmethoxy)phenyl]ethanone. To a stirred solution of l-(5-benzyloxy-2-hydroxyphenyl)ethanone (3.0 g, 12.4 mmol) in anhydrous DMF (15 ml) was added NaH (0.55 g, 13.6 mmol). The mixture was allowed to stir at RT for 30 min and then heated to 60 C. A solution of (i?)-oxiran-2- ylmethyl 4-methylbenzenesulfonate (2.83 g, 12.4 mmol) in DMF was added dropwise at 60 C during 1 h. Stirring was then continued at 60 C for 3 h. The cooled reaction was quenched by addition of water (80 ml) and extracted three times with EtOAc. The combined organic layers were extracted twice with aq 1 M NaOH and washed with water and brine. The organic layer was dried with Na2SO4 and concentrated. The crude product obtained was purified by column chromatography with EtO Ac/toluene as eluent to afford the title compound (2.35 g) as a white solid.1H NMR (CDCl3): delta 2.67 (s, 3H), 2.75 (m, IH), 2.93 (t, IH), 3.37-3.40 (m, IH), 3.96 (dd, IH), 4.32 (dd, IH), 5.04 (s, 2H), 6.89 (d, IH), 7.08 (dd, IH), 7.32-7.43 (m, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3h; | General procedure: To a DMF (25mL) solution of 2-hydroxy-5-methoxybenzaldehyde (2.0g, 13.2mmol) were added potassium carbonate powder (2.2g, 15.8mmol) and epichlorohydrin (1.34mL, 17.2mmol). The resulting suspension was heated to 80C for 3h. The reaction mixture was cooled to ambient temperature and added AcOEt and water. The extracts are combined, and washed by brine, then dried over anhydrous Na2SO4. The mixture was concentrated in vacuo and purified by column chromatography (ethyl acetate: petroleum ether=1:10) to give compound22a(1.6g, 58%) as a colorless oil. |
76% | With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 4h; | General procedure: 5-bromosalicylaldehyde (5.0 g, 25 mmol) was dissolved in N,N-dimethylformamide (80 mL). add potassium carbonate (6.91 g, 50 mmol) and epichlorohydrin (2.94 mL, 37.5 mmol) was heated to 80 ° C and stirred for 4 h. The reaction was monitored by TLC (petroleum ether / ethyl acetate = 5/1). After the reaction mixture was completed, it was cooled to room temperature, diluted with water and extracted twice with ethyl acetate. The organic phase was combined, washed with water and brine, dried over anhydrous sodium sulfate. Filtered and the solvent was evaporated and the crude product purified by column chromatography (petroleum ether / ethyl acetate = 10/1), After purification, 3.2 g of a colorless liquid was obtained in a yield of 50percent. |
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