N-(tert-butoxycarbonylamino)-phenylalanine → (3R,4S)-3-amino-1-(2-amino-3-phenylpropyl)-4-(3-boronopropyl)pyrrolidine-3-carboxylic acid

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Reaction Steps

(3R,4S)-3-Amino-1-(2-amino-3-phenylpropyl)-4-[3-(dihydroxyboryl)propyl]pyrrolidine-3-carboxylic acid trihydrochloride (mixture of two diastereomers; each a racemate) is prepared in a manner analogous to that set forth in Example 54, Steps 1-3 except commercial N-(tert-butoxycarbonylamino)-phenylalanine is used in place of tert-butyl 7-chloro-3-(hydroxymethyl)-3,4-dihydroisoquinoline-2(1 H)-carboxylate. 1H NMR (0.1M DCl in D2O, 400 MHz) δ 7.30 (m, 5 H), 4.41 (s, 2 H), 4.00 (m, 3 H), 3.85 (m, 2 H), 3.75 (m, 1 H), 3.41 (m, 2 H), 2.86 (m, 1 H), 2.69 (m, 1 H), 1.60 (m, 1 H), 1.27 (m, 3 H), 0.67 (m, 2 H). ESI+ MS found for C17H28BN3O4 m/z 332.2 (M−18+H), 314.2 (M−36 (2H20)+H); ESI− MS m/z 330.2 (M−18 (H20)−H).

Provenance & Evidence