反应详情

In a hydrogenation reactor, (S)-methyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-nitrophenyl)propanoate (3B; 25 g, 56 mmol) was dissolved in THF (200 mL), and 15 mL of 4N HCl was added to the reaction mixture. Then, 10% Pd/C (2.5 g) was added to the reaction mixture. Hydrogen was introduced into the reactor until pressure reached 4 MPa. The reaction was stirred at room temperature for 1 hour. The catalyst was removed by filtration and washed with THF. The pH of the solution was adjusted to about 7 by adding saturated NaHCO3 (aq) while the solution was on an ice bath. The organic layer was separated, and the aqueous layer was washed with CH2Cl2 (2×15 mL). The combined organic fractions were dried with anhydrous Na2SO4 to give a solution of (S)-methyl 2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4-aminophenyl)propanoate 3C. The solution was used directly in step 3.

1. customThe catalyst was removed by filtration
2. washwashed with THF
3. additionby adding saturated NaHCO3 (aq) while the solution
4. customwas on an ice bath
5. customThe organic layer was separated
6. washthe aqueous layer was washed with CH2Cl2 (2×15 mL)
7. dry with materialThe combined organic fractions were dried with anhydrous Na2SO4