3-Hydroxy-3-phenylpropanehydrazide → 5-{(2S)-2-({(2S)-2-[(tert-Butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-[2-(3-hydroxy-3-phenylpropanoyl)hydrazino]-3-oxopropyl}-2-(carboxymethoxy)benzoic Acid

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Reaction Steps

Synthesis was performed from (2S)-2-({(2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoyl}amino)-3-[3-(methoxycarbonyl)-4-(2-methoxy-2-oxoethoxy)phenyl]propanoic acid (100 mg, 0.18 mmol) and 3-phenylhydracrylic acid hydrazide (39 mg, 0.22 mmol) according to Method C with HPLC purification to give the title compound (58 mg) as a diasteromeric mixture. 1H-NMR (400 MHz, CD3OD) d 7.77 (1H), 5.11 (dd, J=4.6 Hz, J=8.6 Hz, 1H), 4.78 (2H), 4.70 (m, 1H), 4.24 (dd, J=5.0 Hz, J=9.3 Hz, 1H), 1.34 (s, 9H); IR (KBr) 3274, 1681, 1652, 1608 cm−1; HRMS m/z 692.2670 (calc. of monoisotopic mass for C35H40N4O11 gives 692.2694).

Provenance & Evidence