Diisopropylethylamine → HCID 70946581, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of [2-(benzyloxy)-5-((1R)-2-bromo-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl) phenyl]methanol (preparation 23), (3.4 g, 7.5 mmol), [3-(2-amino-2-methylpropyl)phenyl]acetic acid (preparation 146), (1.7 g, 7.5 mmol) and N,N-diisopropylethylamine (1.4 mL, 8 mmol) in dimethylsulfoxide (7.5 mL) was stirred at 90° C. for 28 hours. The reaction mixture was then cooled, diluted with ethyl acetate and washed with water. The organic solution was then dried over magnesium sulfate, concentrated in vacuo and the residue was purified by column chromatography on silica gel, eluting with ethyl acetate:pentane, 66:33, to afford the title compound as a colourless oil in 50% yield, 2.2 g. 1H NMR (400 MHz, CDCl3) δ: 7.44-7.31 (6H, m), 7.30-7.19 (3H, m), 7.13-7.05 (2H, m), 6.80 (1H, d), 4.75-4.66 (3H, m), 3.68 (3H, s), 3.59 (2H, s), 2.90-2.72 (4H, m), 1.22-1.09 (6H, m), 0.70 (9H, s), −0.06 (3H, s), −0.28 (3H, s) ppm.

Provenance & Evidence