Sodium Hydroxide → 3-(2-(3-(Benzyloxy)-5-bromopyridin-2-ylamino)thiazol-4-yl)propanoic acid

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Reaction Steps

Methyl 3-(2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazol-4-yl)propanoate (Example 58; 1.500 g, 3.346 mmol) was dissolved in THF (50 mL) and water (25 mL), followed by the addition of sodium hydroxide (0.2676 g, 6.691 mmol), and the mixture was at ambient temperature for 16 hours. The mixture was concentrated, and partitioned between DCM and saturated aqueous NH4Cl. The layers were separated and the aqueous was extracted with DCM/THF and then 100% THF. The combined organics were dried over Na2SO4, filtered and concentrated to give 3-(2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazol-4-yl)propanoic acid (1.42 g, 98% yield) as white solids. 1H NMR (DMSO-d6) δ 2.58 (t, J=7.6 Hz, 2H), 2.82 (t, J=7.6 Hz, 2H), 5.29 (s, 2H), 6.65 (s, 1H), 7.35 (t, J=7.2 Hz, 1H), 7.41 (t, J=7.2 Hz, 2H), 7.58 (s, 1H), 7.60 (s, 1H), 7.62 (d, J=2.0 Hz, 1H), 7.96 (d, J=1.8 Hz, 1H); Mass Spectrum (apci) 434 (M+H).

Provenance & Evidence