Triethylamine → HCID 11628462, compound

Participants

Reaction Steps

Compound 23 (527 g, 1.18 mmol) was dissolved in CH2Cl2 (10 mL) containing MS (4 Å). Benzyl N-(2-hydroxyethyl) carbamate (300 mg, 1.54 mmol) was added and the mixture was stirred under argon at −20° C. for 30 min before NIS (345 mg, 1.53 mmol) and AgOTf (cat) was added. After 30 min the reaction mixture was neutralized with Et3N, diluted with CH2Cl2, washed with Na2S2O3 (10%), filtered (silica) and concentrated. Chromatography (1:0→1:1 toluene-EtOAc) gave 24 (595 mg, 1.02 mmol, 86%); [α]D+46° (c 1.0, CHCl3); 13C NMR δ −5.38, −5.34 (CH3Si), 18.4 ((CH3)3CSi), 20.6, 20.8 (CH3CO), 25.9 ((CH3)3CSi), 40.7 (HOCH2CH2NH), 61.6, 62.6, 66.6, 66.9, 67.6, 71.3, 71.8 (C-2-6, PhCH2O, OCH2CH2N), 98.0 (C-1), 128.2, 128.3, 128.6, 136.5 (aromatic C), 156.4 (NHCOOCH2), 169.6, 170.1 (CH3CO); 1H NMR δ 0.03 (s, 3H), 0.04 (s, 3H), 0.89 (s, 9H), 2.03 (s, 3H), 2.09 (s, 3H), 2.35 (s, 1H) 3.32-3.40 (m, 1H), 3.44-3.52 (m, 1H), 3.58-3.66 (m, 3H), 3.72-3.80 (m, 2H), 3.98-4.00 (m, 1H), 5.11 (s, 2H), 5.18-5.23 (m, 1H), 5.32-5.36 (m, 1H), 7.16-7.36 (m, 5H).

Provenance & Evidence