Acetic Acid → HCID 54401251, compound

Participants

Reaction Conditions

Reaction Steps

A solution comprised of 2-bromopyridine (0.291 mL, 3.06 mmol) in dry THF (2 mL) was cooled to −78° C. and then a solution of n-butyllithium (1.6 mL, 2.72 mmol) in pentane was added dropwise over 2 minutes. The mixture was stirred at −78° C. for 10 minutes and then a solution of benzyl 1-[1-(N-methoxy-N-methylcarbamoyl)-3-phenylpropylcarbamoyl]-3-methylbutylcarbamate (0.3 g, 0.64 mmol) in THF (2 mL) was added slowly. The mixture was stirred, while allowing to slowly warm to room temperature, and then poured into a solution comprising acetic acid (0.163 mL) in diethyl ether (50 mL). The organic phase was washed with brine (40 mL), dried (MgSO4) and concentrated in vacuo. Product was purified from the residue by flash chromatography on silica gel eluting with 1:2 ethyl acetate/hexanes to provide benzyl 3-methyl-1-(1-pyrid-2-ylcarbonyl-3-phenylpropylcarbamoyl)butylcarbamate (82 mg, 0.17 mmol) as a white solid. MS (ESI) m/z=488 (M+1); 1H NMR (CDCl3): δ 0.8-1.05 (d, J=4 Hz, 6H), 1.5 (m, 1H), δ 1.6-1.78 (t, 2H), δ 1.99-2.20 (m, 1H), δ 2.6-2.9 (m, 1H), δ 2.55-2.85 (m, 2H), δ 4.25 (m, 1H), δ 5.17 (s, 2H), δ 5.25 (m, 1H), δ 6.00 (m, 1H), δ 6.85-6.95 (d, J=10 Hz, 1H), δ 7.1-7.4 (m, 10H) 7.50(t, J=4 Hz, 1H), δ 7.85 (t, J=6 Hz, 1H) 8.01 (d, J=8 hz, 1H), δ 8.69 (m, 1H). Anal (C29H33N3O4).

Provenance & Evidence