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

Participants

Reaction Conditions

Reaction Steps

A solution of 2C (8.5 g, 28 mmol) in DMF (30 mL) was added with an. K2CO3 (1.5 mol eq, 5.99 g) and, after few minutes, iodomethane (1.2 mol eq, 3.21 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 (150 mL) and the aqueous phase extracted with EtOAc (3×60 mL). The combined organic phases were dried over Na2SO4 and evaporated under reduced pressure to afford 3C as a pale yellow oil (8.6 g, 97% yield). 1HNMR (DMSO, 200 MHz) δ 2.88 (s, 3H), 3.52 (s, 3H), 3.66 (m, 2H), 4.02 (q, 1H, J=6), 4.602 (t, 1H, J=6.1), 5.11 (t, 1H), 7.64 (d, 2H), 7.76 (d, 2H).

Provenance & Evidence