N-Hydroxyphthalimide → HCID 59873668, compound

Participants

Reaction Steps

A mixture of tert-butyl (2S)-3-[4-(3-hydroxypropoxy)phenyl]-2-[(phenylmethoxy)carbonylamino]propanoate (0.215 g, 0.5 mmol), as prepared in the preceding step, N-hydroxyphthalimide ((0.098 g, 0.6 mmol), and triphenylphosphine (0.157 g, 0.6 mmol) in anhydrous tetrahydrofuran (10 mL) was treated with diethyl azodicarboxylate (0.095 g, 0.6 mmol). The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was evaporated to dryness and the residue was placed on a silica gel column (10 g Waters Sep-Pak) and eluted with 20% ethyl acetate and 80% hexane. The pure fractions were combined and evaporated to give the title compound (0.280 g, 97% yield). 1H NMR (300 MHz, CDCl3) δ7.84 (dd, J=5.6,3.0 Hz, 2H), 7.75 (dd, J=5.6, 3.0 Hz, 2H), 7.28-7.34 (m, 5H), 7.03 (d, J=8.7 Hz, 2H), 6.83 (d, J=8.7 Hz, 2H), 5.22 (br d, J=8.2 Hz, 1H), 5.09 (d, J=2.5 Hz, 2H), 4.48 (m, 1 H), 4.41 (t, J=6.3 Hz, 2H), 4.20 (t, J=6.2 Hz, 2H), 3.01 (br d, J=5.9 Hz, 2H), 2.23 (p, J=6.2 Hz, 2H), 1.41 (s, 9H).

Provenance & Evidence