Divinyl sulfone → 1,1-Dimethylethyl N-((1S)-2-(methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl)carbamate

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Boc-Phe-N(OCH3)CH3 was prepared from Boc-Phe-OH and N,O-dimethylhydroxylamine hydrochloride using standard mixed anhydride coupling procedure, yield 93%. 1H-NMR (CDCl3) δ 1.4 (s, 9H, Boc), 2.8-2.9 (m, 1H, CH2-Phe), 3.0-3.1 (m, 1H, CH2-Phe), 3.2 (s, 3H, N—CH3), 3.6 (s, 3H, O—CH3), 4.9 (m, 1H, α-H), 5.2 (b, 1H, NH), 7.1-7.3 (m, 5H, Ph). MS (FAB+) m/z 309 (M+1, 30%), 253 (M−tBu+1, 100%). Reduction of Boc-Phe-N(OCH3)CH3 with lithium aluminum hydride according to a previous method described in J. A. Fehrentz et al., Synthesis (1983), 8, 676 gave Boc-Phe-H, yield 88%. 1H-NMR (CDCl3) δ 1.4 (s, 9H, Boc), 3.1 (d, 2H, CH2-Phe), 4.4 (m, 1H, α-H), 5.0 (b, 1H, NH), 7.1-7.3 (m, 5H, Ph), 9.6 (s, 1H, CHO). MS (FAB+) m/z 250 (M+1, 15%), 150 (M−Boc+1, 100%).

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