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

Participants

Reaction Conditions

Reaction Steps

A solution of 2A (1 g, 3.6 mmol) in DMF (15 mL) was added with an. K2CO3 (1.4 mol eq, 0.7 g) and, after few minutes, 2-iodoethane (1.2 mol eq, 0.45 ml) was added and the mixture heated at 50° C. for 5 h. The solvent was removed under reduced pressure, water was added to the residue (80 mL) and the aqueous phase extracted with EtOAc (3×30 mL). The combined organic phases were dried using Na2SO4 and evaporated under reduced pressure to obtain 3B as a pale yellow oil (1.1 g, quantitative yield). 1HNMR (DMSO, 200 MHz) δ 1.13 (t, 3H, J=8), 3.29 (q, 2H), 3.41 (s, 3H), 3.79 (m, 2H), 4.53 (t, 1H), 5.14 (t, 1H), 7.41 (t, 2H, J=10), 7.86 (m, 2H).

Provenance & Evidence