benzyl (2S)-2-[[(2S)-3-(difluoromethoxy)-2-[(2-morpholinoacetyl)amino]propanoyl]amino]-3-phenyl-propanoate → (2S)-2-[[(2S)-3-(difluoromethoxy)-2-[(2-morpholinoacetyl)-amino]propanoyl]amino]-3-phenyl-propanoic acid

Participants

Reaction Steps

A stirred solution of benzyl (2S)-2-[[(2S)-3-(difluoromethoxy)-2-[(2-morpholinoacetyl)amino]propanoyl]amino]-3-phenyl-propanoate (1.54 g, 2.96 mmol) in THF (10 mL) was treated with palladium (10 wt. % on activated carbon) (157 mg, 0.148 mmol) and stirred under an atmosphere of hydrogen, balloon pressure, for 1 h. The mixture was then filtered through a pad of Celite™ and concentrated in vacuo giving the compound of Formula XVIII(a) (1.27 g, quantitative yield) as colourless foam. 1H NMR (CDCl3, 400 MHz): δ (ppm) 8.09 (m, 1H), 7.24-7.05 (m, 5H), 6.10 (t, J=74 Hz, 1H), 5.6 (brs, 1H), 4.70-4.60 (m, 2H), 4.15-4.01 (m, 1H), 3.95-3.85 (m, 1H), 3.70-3.55 (m, 4H), 3.25-2.90 (m, 4H), 2.65-2.50 (m, 4H).

Provenance & Evidence