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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. : | 111061-55-3 |
Formula : | C38H33NO5 |
M.W : | 583.67 |
SMILES Code : | O=C(O)[C@H](CCOC(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3)NC(OCC4C5=CC=CC=C5C6=CC=CC=C46)=O |
MDL No. : | MFCD00270544 |
InChI Key : | QUTREFXHXPNEJN-DHUJRADRSA-N |
Pubchem ID : | 11387678 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-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 |
---|---|---|
81% | With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 3h; | To a stirred solution of (4-(5-heptyl-1,2,4-oxadiazol-3- yl)phenyl)methanamine (LX, prepared with procedures similar to that described in Example 79) (0.290 g, 1.20 mmol) and (S)-2-(((9No.-fluoren-9-yl)methoxy)carbonylamino)-4- (trityloxy)butanoic acid (0.841 g, 1.44 mmol) in dichloromethane (6 mL) was added N-(3- dimethylaminopropyl)--V-ethylcarbodiimide hydrochloride (0.282 g, 1.44 mmol). The reaction mixture was allowed to stir at room temperature. After 3 hours, the reaction mixture was diluted with dichloromethane and washed with IN hydrochloric acid. The organic phase was dried (sodium sulfate), filtered, and concentrated to provide a yellow oil. Flash chromatography using an Isco Combiflash unit (40 g Sitheta2 column, 30-50% ethyl acetate/hexanes) afforded 0.807 g (81%) of(5)-(9H-fluoren-9-yl)methyl l-(4-(5-heptyl-1,2,4-oxadiazol-3-yl)benzylamino)-1-oxo- 4-(trityloxy)butan-2-ylcarbamate (LXI) as a yellow solid: 1H NMR (CDCl3) delta 8.00-7.95 (m, 2H), 7.76-7.70 (m, 2H), 7.53-7.47 (m, 2H), 7.42-7.33 (m, 8H), 7.30-7.17 (m, 13H), 6.56 (br s, 1H), 6.04 (d, J= 6 Hz, 1H), 4.45-4.28 (m, 5H), 4.19-4.12 (m, 1H), 3.40-3.24 (m, 2H), 2.93 (t, J= 7.6 Hz, 2H), 2.19-2.01 (m, 2H), 1.92-1.81 (m, 2H), 1.48-1.23 (m, 8H), 0.89 (t, J= 6.9 Hz, 3H) ppm. |