(Diethylamino)sulfur trifluoride → HCID 54398697, compound

Participants

Reaction Conditions

Reaction Steps

A stirred mixture of the product from Step 11 (0.085 g, 0.255 mmol)) and CH2Cl2 (10 ml), under nitrogen is cooled to −70° C. and treated, dropwise stirring 2 min, with a solution of (diethylamino)sulfur trifluoride (0.07 ml, 0.53 mmol) in CH2Cl2 (1 ml). The mixture is allowed to warm to ambient temperature slowly during 3 h. Additional CH2Cl2 (10 ml) is added and the mixture is kept at ambient temperature for 20 h, cooled to −70° C. and treated with 0.07 ml of additional DAST. It is kept at −70° C. for 1 h and at ambient temperature for 4 h, mixed with ice cold, saturated NaHCO3 and extracted with EtOAc. The extracts are washed with water and brine, dried (MgSO4) and concentrated. Chromatography of the residue on silica gel with 3.5% MeOH—CH2Cl2 gave 0.036 g of the titled product: HRMS (FAB) calcd for C16H18FN3O4+H 336.1359, found 336.1351; 1H NMR [300 MHz, (CD3)2SO] δ1.81 (s, 3H), 2.85, 3.00 (m, m, 1H), 3.38 (m, 3H), 3.71 (m, 1H), 4.06 (m, 1H), 4.30-4.88 (m, 4H), 7.30 (m, 1H), 7.43, 7.87 (d, d, 1H), 7.50 (m, 1H), 8.23 (t, 1H), 8.45, 9.00 (s, s, 1H).

Provenance & Evidence