Methyl iodide → methyl (2S)-3-hydroxy-2-(methyl(p-tolylsulfonyl)amino)propanoate

Participants

Reaction Conditions

Reaction Steps

A solution of 2E (2 g, 7.35 mmol) in DMF (15 mL) was added with an .K2CO3 (1.5 mol eq, 1.52 g) and, after few minutes, iodomethane (1.2 mol eq, 0.81 ml) was added and the mixture was heated at 50° C. overnight. The solvent was removed under reduced pressure, water was added to the residue (120 mL) and the aqueous phase was extracted with EtOAc (3×50 mL). The combined organic phases were dried over Na2SO4 and evaporated under reduced pressure to afford 3E as a pale yellow oil (2.1 g, quantitative yield). 1HNMR (DMSO, 200 MHz) δ 2.38 (s, 3H), 2.87 (s, 3H), 3.64 (s, 3H), 3.70 (t, 2H), 4.58 (t, 1H), 5.11 (t, 1H), 7.40 (d, 2H, J=8), 7.61 (d, 2H, J=8).

Provenance & Evidence