Sodium Hydroxide → HCID 10781998, compound

Participants

Reaction Steps

A mixture of the title compound of Example 2A (519.6 g, 2.564 mol) and tert-butyl bromoacetate (500 g, 2.564 mol) was added dropwise over 30 min to a stirred mixture of 10N aqueous NaOH (2.56 L, 25.6 mol) and benzyltriethylammonium chloride (2.56 g, 11.2 mmol) at 10°. The reaction mixture was stirred at room temperature for 2 h and then diluted with Hex (750 mL). The organic phase was separated and washed serially with H2O (100 mL) and brine (2×100 mL), dried (MgSO4), and concentrated under reduced pressure to give the title compound (822 g, 100% yield) which was used without further purification for the next step (Example 2C). 1H NMR (400 MHz, CDCl3) δ5.32 (d, J=1.4 Hz, 1H), 5.20 (broad s, 1H), 3.75 (s, 6H), 3.25 (broad s, 2H), 3.06 (s, 2H), 1.43 (s, 9H). MS (FAB) m/z 321 (MH+).

Provenance & Evidence