4-(4-(3-Cyano-4-(ethylsulfonyl)phenylamino)-4-oxobutyl)phenylboronic acid → (S)-4-(2-(3-(1-(benzyloxycarbonylamino)-3-ethoxy-3-oxopropyl)phenylcarbamoyloxy)ethyl)-3-methylphenylboronic acid

Participants

Reaction Steps

Using a procedure analogous to that used to prepare 6D, 34D (800 mg, 1.37 mmol) was reacted with 5,5′,5′-tetramethyl-[2,2′]bi[[1,3,2]dioxaborinanyl] to give 34E (530 mg, 70%) as an oily brown solid. 1H NMR (400 MHz, MeOD) δ ppm 1.16 (t, J=7.20 Hz, 3 H) 2.36 (s, 3 H) 2.67-2.85 (m, 2 H) 3.01 (t, J=7.07 Hz, 2 H) 4.06 (q, J=7.16 Hz, 2 H) 4.31 (t, J=7.07 Hz, 2 H) 4.96-5.11 (m, J=12.55, 12.55, 12.55 Hz, 3 H) 6.99 (d, J=7.33 Hz, 1 H) 7.15-7.25 (m, J=7.83, 7.83 Hz, 3 H) 7.31 (s, H) 7.35-7.43 (m, 3 H).

Provenance & Evidence