P-Toluenesulfonylhydrazide → HCID 18512161, compound

Participants

Reaction Steps

The product from Example 44D (0.040 g, 0.102 mmoles) and p-toluenesulfonhydrazide (0.150 g, 1.02 mmoles) in ethylene glycol dimethyl ether (5 mL) at reflux were treated dropwise over a four hour period with a solution of sodium acetate trihydrate (0.232 g, 1.70 mmoles) in water. After the addition, the reaction mixture was allowed to cool to room temperature, poured into water and extracted with methylene chloride (3×). The extracts were combined, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by preparative HPLC (CH3CN:0.1% TFA in H2O) on a YMC ODS Guardpak column. 1H NMR (300 MHz, CDCl3) δ7.32 (dd, J=8.0, 1.2 Hz, 1H), 7.35-7.15 (m, 11H), 7.09 (dd, J=8.0, 1.2 Hz, 1H), 6.14 (s, 1H), 4.09 (s, 4H), 2.85 (s, 3H), 2.74 (q, J=7.6 Hz, 2H), 1.00 (t, J=7.6 Hz, 3H); MS (ESI+) m/z 395 (M+H)+.

Provenance & Evidence