Structure of 4720-83-6
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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. : | 4720-83-6 |
Formula : | C7H8O2 |
M.W : | 124.14 |
SMILES Code : | O=C1OC2C=CCC1C2 |
MDL No. : | MFCD09038751 |
InChI Key : | TVEXGJYMHHTVKP-UHFFFAOYSA-N |
Pubchem ID : | 376759 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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 sodium hydrogencarbonate; for 3h;Reflux; | To a solution of compound 3 (58 g) in MeOH (800 ml) was added NaHC03 (47 g) with stirring. The reaction mixture was stirred under gentle reflux for 3h, cooled to room temperature, filtered and concentrated to dryness. The residue was dissolved in EtOAc (300 ml) and washed with H20. Aqueous layer was extracted with EtOAc (3x100 ml). Combined organic layers (600 ml) were washed with 0.5M HC1 (200 ml), H20 (100 ml), and brine (100 ml), dried (Na2S04), filtered, and concentrated to dryness. The residue was purified by column chromatography (Si02, Hexanes-EtOAc 3: 1?3:2) to give compound 4 (54g). Purity: >95% by TLC. | |
54 g | With sodium hydrogencarbonate; for 3h;Reflux; | To a solution of compound 3 (58g) in MeOH (800ml) was added NaHCO3 (47g) with stirring. The reaction mixture was stirred under gentle reflux for 3h, and then cooled to room temperature, filtered and concentrated to dryness. The residue was dissolved in EtOAc (300ml) and washed with 30. Aqueous layer was extracted with EtOAc (3x100ml). Combined organic layers (600ml) were washed with 0.5M HQ (200ml), H20 (100ml), and brine(100ml)5 dried ( aaSOTh then filtered, and concentrated to dryness. The residue was purified by column chromatography (SiO?, Hexanes-EtOAc 3; ?3;2) to give compound 4 (54g), Purity: >95% by TLC |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In xylene; for 16h;Heating / reflux; | To 6-oxabicyclo [3.2. 1] oct-3-en-7-one (2.6 g, 21 mmol) in xylenes (50 ml) under nitrogen was added benzylamine (3.42 g, 32 mmol). The mixture was heated under reflux for 16 h, then cooled to room temperature. The heavy white precipitate was collected by filtration, and recrystallized from dichloromethane/hexane to give the amide as a white solid (3.8 g, 78%, m. p. 127- 128C) |
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