Sodium Iodide → HCID 10648076, compound

Participants

Reaction Steps

To a solution of methyl (2S)-3-[(methylsulfonyl)oxy]-2-(tritylamino)propanoate CII (22 g; 0.05 mol) in acetone (700 mL) was added sodium iodide (150 g; 1.0 mol) and stirred at r.t. for one week under argon. The acetone was evaporated and the residue was dissolved in diethyl ether (1.5 L). The solids were filtered and the solvent reduced to 1 L before washing with 10% aq Na2S2O3 (3×) and water (200 mL). The solvent was removed under reduced pressure and the residue purified on a silica gel column (10:1→2:1 hexane/EtOAc) and then crystallized from hexane. The methyl (2R)-3-iodo-2-(tritylamino)propanoate CIII was obtained as yellow foam (21 g; 0.045 mol; 89% yield). 1H NMR (CDCl3) [2.25-2.28 (m, 1st rotamer), 2.89 (d, J=10 Hz, 2nd rotamer), 1H], [2.54 (dd, J=13 Hz, J=6 Hz), 3.21 (dd, J=10 Hz, J=8 Hz), 1st rotamer, 1H], [2.69 (dd, J=12 Hz, J=8 Hz), 3.35 (dd, J=10 Hz, J=3 Hz), 2nd rotamer, 1H], [3.31 (s, 1st rotamer), 3.77 (s, 2nd rotamer), 3H], [3.48 (ddd, J=10 Hz, J=7 Hz, J=3 Hz, 2nd rotamer), 4.39 (dd, J=8 Hz, J=6 Hz, 1st rotamer), 1H], 7.18-7.22 (m, 3H), 7.29 (dd, J=8 Hz, J=7 Hz, 6H), [7.45 (d, J=8 Hz, 1st rotamer), 7.50 (d, J=8 Hz, 2nd rotamer), 6H].

Provenance & Evidence