(3S)-3-Amino-4-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic Acid Tert-Butyl Ester → (S,S)-3-[2-(7-trifluoromethyl-1-oxo-1H-isoquinolin-2-yl)-butyrylamino]-4-oxo-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic Acid

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Reaction Steps

This compound was prepared using (S)-2-(7-trifluoromethyl-1-oxo-1H-isoquinolin-2-yl)-butyric acid (prepared as described in methods A-E, see example 2) and (3S)-3-amino-4-hydroxy-5-(2,3,5,6-tetrafluoro-phenoxy)-pentanoic acid tert-butyl ester (prepared as described in methods N-P) using procedures similar to those described in methods F, G and E. The product was isolated as a white solid (90% last step). IR (solid) 1791.6, 1649.5, 1516.8, 1493.1, 1322.5 cm−1; 1H NMR (400 MHz, d6-DMSO) δ 0.85 (3H, t), 1.90-2.20 (2H, 2×m), 2.50-2.90 (2H, 2×m), 4.70 (1H, m), 5.25 (2H, dd), 5.45 (1H, m), 6.80 (1H, d), 7.65 (1H, m), 7.70 (1H, d), 7.95 (1H, d), 8.05 (1H, d), 8.45 (1H, s), 9.00 (1H, d) ppm; 19F NMR (376 MHz, d6-DMSO) (proton decoupled) δ −56.60, −70.15, −136.38, −152.08.

Provenance & Evidence