3-{4-[4-(2-Tert-butoxycarbonylamino-2-carboxy-ethyl)-phenoxy]-phenyl}-acrylic acid methyl ester → 2-Tert-butoxycarbonylamino-3-{4-[4-(2-methoxycarbonyl-ethyl)-phenoxy]-phenyl}-propionic acid

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Reaction Steps

Raney nickel 2800 (15.4 g) was added to a degassed solution of the unsaturated ester 3 (14.7 g) in MeOH (100 mL) and the resulting suspension was treated with hydrogen at atmospheric pressure for 18 h. The suspension was filtered over a Celite® bed and concentrated. Flash chromatography (30-50% ethyl acetate in hexane containing 1% acetic acid) of the resulting residue gave the desired saturated ester 4 (8.1 g, 55%). 1H NMR (400 MHz, DMSO-d6): 12.7 (br, 1H), 7.22 (overlapped d, J=8.4 Hz, 4H), 7.08 (d, J=8.0 Hz, 1H), 6.88 (overlapped d, J=8.0 Hz, 4H), 4.07 (br, 1H), 3.00 (m, 1H), 2.82 (t, J=7.6 Hz, 2H), 2.79 (m, 1H), 2.62 (t, J=8.0 Hz, 2H), 1.33 (s, 9H).

Provenance & Evidence