反应详情

To a stirred solution of 2′-methoxy-2-methyl-biphenyl-4-carboxylic acid (0.250 g; 1.032 mmol) in dichloromethane (20 mL) was added one drop of N,N-dimethylformamide followed by dropwise addition of oxalyl chloride (0.144 mL; 1.65 mmol). After stirring for one hour, the mixture was thoroughly evaporated to give the crude acid chloride as a brown oil. The acid chloride then was dissolved in dichloromethane (5 mL) and slowly added to a solution of 10,11-dihydro-5H-pyrrolo [2,1-c][1,4] benzodiazepine (0.57 g, 3.10 mmol) and N,N-diisopropylethyl amine (0.79 mL, 4.53 mmol) in dichloromethane (15 mL). After stirring for 1 hour, the reaction was quenched with water. The organic layer was washed with 1 N hydrochloric acid, 1 N sodium hydroxide and brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give a yellow foam. Purification by flash chromatography using a solvent gradient of 5 to 15% ethyl acetate in hexane yielded a white foam which crystallized upon sonication in ethanol/hexane to give 0.42 g of the desired title product as a white solid, m.p. 133-135° C. MS [(+)ESI, m/z]: 409 [M+H]+. Anal. Calcd. for C27H24N2O2: C, 79.39; H, 5.92; N, 6.86. Found: C, 79.16; H, 5.87; N, 6.90.

1. customthe mixture was thoroughly evaporated
2. customto give the crude acid chloride as a brown oil
3. stirringAfter stirring for 1 hour
4. customthe reaction was quenched with water
5. washThe organic layer was washed with 1 N hydrochloric acid, 1 N sodium hydroxide and brine
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto give a yellow foam
10. customPurification by flash chromatography
11. customyielded a white foam which
12. customcrystallized upon sonication in ethanol/hexane