HCID 11628462, compound → HCID 11705399, compound

Participants

Reaction Steps

To a solution of compound 24 (575 mg, 0.99 mmol) in THF (5 mL), TREAT-HF (0.81 mL, 4.97 mmol) was added. The mixture was stirred under argon at rt overnight. Concentration and chromatography (2:1→0:1 toluene-EtOAc) gave 25 (448 mg, 0.96 μmmol, 97%); [α]D+60° (c 1.0, CHCl3); 13C NMR δ 20.7, 20.8 (CH3CO), 40.7 (HOCH2CH2NH), 61.4, 61.6, 66.4, 67.0, 67.5, 70.9, 71.0 (C-2-6, PhCH2O, OCH2CH2N), 98.2 (C-1), 128.3, 128.3, 128.7, 136.5 (aromatic C), 156.5 (NHCOOBn), 170.1, 170.5 (CH3CO); 1H NMR δ 2.04 (s, 3H), 2.1 (s, 3H), 3.32-3.46 (m, 2H), 3.54-3.60 (m, 2H), 3.62-3.78 (m, 3H), 4.02-4.04 (m, 1H), 5.06-5.18 (m, 3H), 5.22-5.28 (m, 1H), 5.36-5.40 (m, 1H), 7.28-7.38 (m, 5H); HRMS calcd for C20H26N4NaO9 [M+Na]+ 489.1597, found 489.1574.

Provenance & Evidence