Trifluoroacetic acid → (S)-5-(2-phenoxymethyl-pyrrolidine-1-sulfonyl)-1H-indole-2,3-dione

Temperature

0 °C

To a solution of 9 (1.46 g, 5.2 mmol) in CH2Cl2 (5 mL) was added trifluoroacetic acid (5 mL) at 0° C. The mixture was stirred at 0° C. for 15 min. After evaporation of the solvent in vacuo, CH2Cl2 (15 mL) and triethylamine (2 mL) were added, then a solution of 6 (1.44 g, 5.9 mmol) in THF (25 mL) was added at 0° C. The reaction mixture was stirred overnight at room temperature. The solvent was evaporated in vacuo, then ethyl acetate (150 mL) was added, washed with water (50 mL×2) and saturated NaCl (50 mL), and dried over Na2SO4. After evaporation of the ethyl acetate, the crude product was purified with ether to afford 1.7 g (84%) of 10 as a yellow solid, mp 204.5-205.9° C. 1H NMR (300 MHz, CDCl3) δ 8.94 (s, 1H), 7.77 (dd, J=8.25 Hz, J=2.1 Hz, 1H), 7.67 (s, 1H), 7.02 (t, J=8.7 Hz, 2H), 6.84 (d, J=8.1 Hz, 1H), 6.69 (t, J=7.2 Hz, 1H), 6.63 (d, J=7.8 Hz, 2H), 3.89 (m, 1H), 3.75-3.66 (m, 2H), 3.23 (m, 1H), 2.96 (m, 1H), 1.72 (m, 2H), 1.54-1.42 (m, 2H). LRMS (FAB) m/e: 387.1 (M+H, 100). Anal. Calcd for C19.N2O5S: C, 59.06, H, 4.70; N, 7.25. Found: C, 58.99, H, 4.74, N, 7.11.

1. customAfter evaporation of the solvent in vacuo, CH2Cl2 (15 mL) and triethylamine (2 mL)
2. additionwere added
3. stirringThe reaction mixture was stirred overnight at room temperature
4. customThe solvent was evaporated in vacuo
5. additionethyl acetate (150 mL) was added
6. washwashed with water (50 mL×2) and saturated NaCl (50 mL)
7. dry with materialdried over Na2SO4
8. customAfter evaporation of the ethyl acetate
9. customthe crude product was purified with ether

ORD record

ord-d227becdb8df4ce79f0b3a00bea9d21e

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08329686B2