反应详情

To a stirred solution of 4-{[(1,1-dimethylethyl)oxy]carbonyl}-2-morpholinecarboxylic acid (500 mg, 2.16 mmol) in dry DMF (2 mL) at 0° C. were added EDCI (456 mg, 2.38 mmol), HOBT (331 mg, 2.16 mmol) and aniline (0.22 mL, 2.38 mmol). The solution was stirred at room temperature overnight. The solvent was evaporated and the resulting residue was poured onto water and extracted with EtOAc (2×) and CH2Cl2 (2×). The combined organics were washed with brine and dried (MgSO4), filtered and evaporated. To this crude material dissolved in CH2Cl2/CH3OH (3 mL/0.3 mL) was added TFA (1.5 mL), and the reaction mixture was stirred at room temperature for 3 hours. The mixture was concentrated and dried in vacuo to afford a light brown oil. Et2O and hexanes were added and a precipitate crashed out. The mixture was sonicated and filtered to afford the title compound (604 mg). LC-MS (ES) m/z=207 [M+H]+.

1. customThe solvent was evaporated
2. additionthe resulting residue was poured onto water
3. extractionextracted with EtOAc (2×) and CH2Cl2 (2×)
4. washThe combined organics were washed with brine
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customevaporated
8. dissolutionTo this crude material dissolved in CH2Cl2/CH3OH (3 mL/0.3 mL)
9. additionwas added TFA (1.5 mL)
10. stirringthe reaction mixture was stirred at room temperature for 3 hours
11. concentrationThe mixture was concentrated
12. customdried in vacuo
13. customto afford a light brown oil
14. customThe mixture was sonicated
15. filtrationfiltered