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

Participants

Reaction Conditions

Reaction Steps

A solution of 2F (3.0 g, 10.8 mmol) in DMF (15 mL) was added with an. K2CO3 (1.5 mol eq, 2.24 g) and, after few minutes, 2-iodoethane (1.2 mol eq, 1.33 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 (4×50 mL). The recombined organic phases were dried over Na2SO4 and evaporated under reduced pressure to afford 3F as a pale orange viscous oil (3.2 g, 95% yield). 1HNMR (DMSO, 200 MHz) δ 1.15 (m, 3H), 2.00 (s, 3H), 3.79 (q, 2H, J=8), 4.06 (t, 1H), 4.59 (t, 1H), 5.18 (m, 2H), 7.94 (m, 4H).

Provenance & Evidence