Sodium Hydroxide → 1-(4-Azidobutanoyl)-4-(1,3-dihydroxypropan-2-yloxy)-7-nitroindoline

Participants

Reaction Steps

A solution of 26 (0.76 g, 1.7 mmol) in MeOH (85 mL), water (8.5 mL) and 1 M aq. NaOH (4.1 mL, 4.1 mmol) was stirred at room temperature for 2 min, quenched with 1 M citric acid (8.5 mL) and concentrated under reduced pressure to ˜20 mL. The solution was diluted with water (30 mL), washed with EtOAc (3×50 mL) and the combined organic washings were washed with saturated aq. NaHCO3 and brine, dried and evaporated to a brown viscous oil which after trituration with Et2O gave 27 (0.49 g, 78%) as yellow needles, mp 78-79° C. (EtOAc-hexanes); 1H NMR (500 MHz) δ 7.70 (d, J=9.2 Hz, 1H), 6.76 (d, J=9.2 Hz, 1H), 4.57 (quintet, J=4.8 Hz, 1H), 4.25 (d, J=8.1 Hz, 2H), 3.95 (dd, J=11.9, 4.8 Hz, 2H), 3.92 (dd, J=11.9, 4.8 Hz, 2H), 3.43 (t, J=6.4 Hz, 2H), 3.14 (t, J=8.0 Hz, 2H), 2.57 (t, J=6.9 Hz, 2H), 2.03 (t, J=7.6 Hz, 2H), 2.02 (quintet, J=6.4 Hz, 2H); HRMS (ESI) (m/z): Calcd for (C15H19N5O6+H)+, 366.1408. Found: 366.1427.

Provenance & Evidence