Methyl iodide → methyl (2S)-2-[(4-fluorophenyl)sulfonyl-methyl-amino]-3-hydroxy-propanoate

Participants

Reaction Conditions

Reaction Steps

A solution of 2A (2 g, 7.2 mmol) in DMF (20 mL) was added with an. K2CO3 (1.5 mol eq, 1.49 g) and, after few minutes, iodomethane (1.2 mol eq, 0.8 ml) was added and the mixture heated at 50° C. for 12 h. The solvent was removed under reduced pressure, water was added to the residue (100 mL) and the aqueous phase extracted with EtOAc (3×40 mL). The combined organic phases were dried over Na2SO4 and evaporated under reduced pressure to obtain 3A as a pale yellow oil (2.3 g, quantitative yield). 1HNMR (DMSO, 200 MHz) δ 2.82 (s, 3H), 3.50 (s, 3H), 3.69 (m, 3H), 4.60 (t, 1H, J=6), 5.12 (t, 1H, J=6.1), 7.44 (m, 2H), 7.83 (m, 2H).

Provenance & Evidence