Ammonium Hydroxide → HCID 68908622, compound

Participants

Reaction Steps

To a solution of Example 9B (0.30 g, 1.0 mmol) and N,N-diisopropylethylamine (0.21 mL, 1.2 mmol) in 5 mL tetrahydrofuran was added o-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 0.41 g, 1.1 mmol). The mixture stirred for 2 hours at ambient temperature, and 5 mL of NH4OH was added and the reaction mixture stirred for an additional 1 hour. The mixture was concentrated under reduced pressure and the residue was dissolved in 10 mL CH2Cl2. NH4Cl (5 mL) was added, the layers were separated and the aqueous layer was extracted 2×5 mL CH2Cl2. The combined organics were dried over anhydrous Na2SO4, filtered, concentrated, and purified via column chromatography (SiO2, 50% hexanes:ethyl acetate) to afford the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.15 (s, 1H), 1.21 (s, 6H), 1.32 (s, 6H), 2.26 (s, 3H), 2.30 (s, 3H), 5.60-5.84 (m, 2H), 11.88 (s, 1H); MS (DCI/NH3) m/z 295 (M+H)+; anal. calculated for C15H22N2O2S: C, 61.19; H, 7.53; N, 9.52. Found: C, 61.28; H, 7.74; N, 9.44.

Provenance & Evidence