Diisopropylethylamine → HCID 49763663, compound

Participants

Reaction Steps

To a solution containing the product from Example 150E (0.22 mmol) in tetrahydrofuran (2.5 mL) were added the product from Example 1F (0.046 g, 0.243 mmol), DEPBT (0.099 g, 0.331 mmol), and N,N-diisopropylethylamine (0.19 mL, 1.09 mmol) and the mixture was stirred at room temperature for 68 hours. The mixture was partitioned between ethyl acetate and 10% Na2CO3 solution. The organic was washed with additional 10% Na2CO3 solution and then brine, dried over MgSO4, filtered and evaporated. The residue was chromatographed on reverse phase HPLC on a C18 column, eluting with a gradient starting with water and ending with methanol to give the title compound (0.108 g, 70% yield). 1H NMR (300 MHz, DMSO-d6), δ ppm 0.79 (s, 9 H), 0.82 (s, 9 H), 1.42-1.59 (m, 2 H), 2.71-2.79 (m, 3 H), 3.48 (s, 3 H), 3.55 (s, 3 H), 3.61-3.67 (m, 1 H), 3.81 (d, J=9.9 Hz, 1 H), 3.91 (d, J=9.6 Hz, 1 H), 4.03-4.20 (m, 2 H), 4.87 (d, J=5.2 Hz, 1 H), 6.64 (d, J=9.6 Hz, 1 H), 6.80 (d, J=9.6 Hz, 1 H), 7.12-7.23 (m, 8 H), 7.50-7.60 (m, 4 H), 7.65 (d, J=5.9 Hz, 2 H), 7.80 (d, J=8.5 Hz, 1 H), 8.61 (d, J=5.9 Hz, 2 H).

Provenance & Evidence