Boc-Tyr-OMe → (2S)-2-amino-3-{4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenyl}propanoic acid

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Reaction Steps

Amino acid Intermediate 54 was prepared as described for the preparation of Intermediate 46. From 187 mg of N-(Boc)-L-Tyrosine methyl ester and 120 mg of Intermediate 8D (with DIAD replacing DEAD) was prepared 116 mg (53% overall yield) of the title compound as a solid. 1H NMR (DMSO-d6, 300 MHz) δ7.89-7.85 (m, 2H), 7.43-7.36 (m, 3H), 7.12 (d, 2H, J=8.5), 6.9 (d, 2H, J=8.5), 4.9 (s, 2H), 3.63 (m, 1H), 3.0 (dd, 1H, J=14.4, 4.5), 2.85 (dd, 1H, J=14.4, 8.1), 2.37 (s, 3H); low resolution MS (ES+)m/e 353.07 (MH+).

Provenance & Evidence