tert-Butyl hydroperoxide → Phenyl-3-(N-carbobenzyloxyleucyl)amino-4-phenylbut-2-enyl Sulfone

Participants

Reaction Steps

Cbz-Leu-D-Phe-VS-Ph was treated with butyllithium and tert-butylhydroperoxide in freshly distilled THF as described with Cbz-Leu-Phe-VS-Ph above to give Cbz-Leu-Phe-AS-Ph (Isomer B) as a white powder, yield 15%. 1H-NMR (CDCl3) δ 0.8-0.9 (2d, 6H, 2×Leu-CH3), 1.4-1.6 (m, 2H, Leu-CH2), 2.06 (m, 1H, Leu-CH), 3.8 (s, 2H, CH2-Phe), 3.9 (d, 2H, CH2—SO2), 4.1 (m, 1H, α-H), 4.8 (t, 1H, CH═), 4.9-5.0 (b, 1H, NH), 5.1 (m, 2H, Cbz), 7.1-7.4 (m, 10H, 2×Ph), 7.5-7.7 (m, 5H, SO2-Ph); 8.4 (b, 1H, NH). MS (ESI) m/z 535 (M+1, 100%). Anal. calcd. for C30H34N2O5S: C, 67.39; H, 6.56; N, 5.43. Found: C, 67.12; H, 6.61; N, 5.33.

Provenance & Evidence