t-Butyl bromide → HCID 54129514, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of Cbz-Hyp-OH (4.854 g, 18 mmol) in DMA (135 ml), benzyltriethylammonium chloride (4.105 g, 18 mmol), K2CO3 (64 g, 46 mmol) and 2-bromo-2-methylpropane (99 ml, 859 mmol) was stirred at 55° C. for 18 hours. The mixture was diluted with iced water and extracted with EtOAc (3×). The organic phase washed with water, 0.5N NaHSO4 solution and brine dried and the solvent in vacuo to yield the title compound as a yellow oil (5.368 g, 98% yield). 1H-NMR (500 MHz, CDCl3) δ 1.33 (s, 5H), 1.47 (s, 4H), 2.01-2.14 (m, 1H), 2.22-2.38 (m, 1H), 3.50-3.72 (m, 2H), 4.34-4.45 (m, 1H), 4.45-4.53 (m, 1H), 5.04-5.20 (m, 2H), 7.22-7.42 (m, 5H). Analytical HPLC 10.14 min. LC-MS (ES+) m/e=322.2 (MH+).

Provenance & Evidence