Benzoic Acid → HCID 86602359, compound

Participants

Reaction Steps

Dissolve (S)-2-tert-butoxycarbonylamino-3-(4-(4-formylphenoxy)phenyl)-propanoic acid methyl ester (3.05 Kg, 7.64 moles) in toluene (18 L). Add benzoic acid (144.9 g), piperidine (87.6 g) and 2,4-thiazolidinedione (1.11 Kg, 20.5) sequentially. Remove water azeotropically for 6 h. Check completion of the reaction by TLC (SiO2 gel, CHCl3-MeOH, 19:1). Distil off half of the solvent and cool down to room temperature, washed with 5% sodium bicarbonate solution, water, brine and dried over anhydrous sodium sulfate. Yield 3.80 Kg, 99.9%, chiral purity 100% ee. 1HNMR (300 MHz, CD3OD): 7.75 (s, 1H), 7.52 (d, J=9.0 Hz, 2H) 7.26 (d, J=8.4 Hz, 2H), 7.26 (d, J=8.4 Hz, 2H), 7.03 (d, J=9.0 Hz, 2H), 6.95 (d, J=9.0 Hz, 2H), 4.38 (m, 1H), 3.71 (S, 3H), 3.12 (dd, J=5.4 and 13.5 Hz, 1H), 2.85 (dd, J=9.3 and 13.5 Hz, 1H), 1.30 (s, 9H).

Provenance & Evidence