Methylamine → HCID 131723110, compound

Participants

Reaction Steps

To a solution of 78 mg (0.15 mmol) of methyl (2S)-3-{4-[3-(1,3-dioxoisoindolin-2-yloxy)propoxy]phenyl}-2-[(phenylmethoxy)carbonylamino]propanoate, as prepared in the preceding step, in 5 mL THF was added 0.4 mL of 2M methylamine solution in THF. The solution was stirred at room temperature for 3 h. The solvent was then removed under reduced pressure. The mixture was chromatographed on a silica gel column using EtOAc/hexanes (3:7 to 7:3 v/v) as eluent to yield 47 mg (80%) of viscous liquid as product: 1H NMR (300 MHz, CDCl3) δ7.38-7.28 (m, 5H), 6.98 (d, J=8.70 Hz, 2H), 6.79 (d, J=8.70 Hz, 2H), 5.20 (d, J=8.20 Hz, 1H), 5.10 (d, J=12.34 Hz, 1H), 5.05 (d, J=12.34 Hz, 1H), 4.60 (m, 1H), 3.99 (t, J=6.30 Hz, 2H), 3.84 (t, J=6.20 Hz, 2H), 3.71 (s, 3H), 3.10-2.97 (m, 2H), 2.05 (quintet, J=6.24 Hz, 2H).

Provenance & Evidence