Sodium Bicarbonate → HCID 69643317, compound

Participants

Reaction Steps

To a flask with tert-butyl 2-(3-((S)-2-amino-3-phenylpropanamido)-5-(2-methylpyridin-4-yl)pyridin-2-yloxy)acetate (78.J) (58 mg, 0.13 mmol) was added thiazole-4-carbaldehyde (15 mg, 0.13 mmol). Dichloromathane was added as the solvent. Then acetic acid, glacial (8 mL, 0.13 mmol) was added followed by sodium triacetoxyborohydride (80 mg, 0.38 mmol). The reaction was stirred at room temperature for 1 hour and worked up with EtOAc and saturated NaHCO3 solution. Reverse phase HPLC purification afforded compound 78 26 mg (37%). 1H NMR (400 MHz, MeOH) δ ppm 8.78-8.96 (m, 2H) 8.45 (d, J=5.48 Hz, 1H) 8.22 (d, J=2.35 Hz, 1H) 7.57 (s, 1H) 7.49 (dd, J=5.48, 1.56 Hz, 1H) 7.36 (d, J=1.96 Hz, 1H) 7.18-7.31 (m, 5H) 4.90 (d, J=3.13 Hz, 2H) 3.87-3.98 (m, 2H) 3.63 (dd, J=8.61, 5.09 Hz, 1H) 3.19 (dd, J=13.89, 4.89 Hz, 1H) 2.92 (dd, J=14.09, 8.61 Hz, 1H) 2.60 (s, 3H) 1.46 (s, 9H).

Provenance & Evidence