Ammonia → HCID 68349533, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-3-(((benzyloxy)carbonyl)amino)-2,2-dimethylbutanoic acid (6.5 g, 23.27 mmol) in THF (60 mL) was added HOBT (3.00 g, 19.60 mmol), EDCI (3.76 g, 19.60 mmol) and DIPEA (10.27 ml, 58.8 mmol) and stirred at 0° C. for 30 min. 3M ammonia in THF (50 ml, 1848 mmol) was added to afford a white suspension. The reaction mixture was allowed to stir for 12 h at RT. Reaction mass was diluted with water (80 ml). The aqueous layer was treated with EtOAC (3×80 ml). The organic layer was dried over Na2SO4 and concentrated under vacuum to get desired crude product. Crude product was purified by column chromatography (60-120 mesh, 30% EtOAc: Pet-Ether) to get desired product as off white solid (2.7 g, 52%). 1HNMR (400 MHz, CDCl3) δ ppm: 1.15-1.17 (d, J=6.8 Hz, 3H), 1.23-1.27 (m, 6H), 3.66-3.76 (m, 1H), 5.10-5.13 (s, 2H), 5.41-5.89 (m, 3H), 7.26-7.36 (m, 5H).

Provenance & Evidence