Trityl chloride → HCID 69284943, compound

Participants

Reaction Steps

A mixture of (S)-39 (5.85 g, 45.3 mmol), trityl chloride (16.04 g, 57.5 mmol), i-Pr2NEt (11.6 mL, 66.6 mmol) and DMAP (0.527 g, 4.31 mmol) in DMF (21 mL) was stirred at r.t for 3 days. Reaction mixture was separated between brine (80 mL) and water (80 mL). The aqueous layer was extracted with AcOEt (4×80 mL). Combined organic solutions were washed with brine, dried (MgSO4), concentrated and separated by SGC with hexane:AcOEt (in gradient, up to 40% AcOEt) to afford (S)-40 as a foam; yield 12.20 g (73%). 1H NMR (250 MHz, CDCl3) δ 1.16-1.34 (m, 1H), 1.58-1.90 (m, 3H), 2.17-2.31 (m, 1H), 2.33-2.47 (m, 1H), 2.94 (t, J=9.1 Hz, 1H), 3.23 (dd, J=9.1, 3.1 Hz, 1H), 3.56-3.68 (m, 1H), 6.21 (s, 1H), 7.21-7.45 (m, 15H).

Provenance & Evidence