Aniline → HCID 20592410, compound

Participants

Reaction Steps

A solution comprised of 2-[2-(2-benzyloxycarbonylamino-4-methylvalerylamino)-1-hydroxy-4-phenylbutyl]oxazole-4-carboxylic acid (0.05 g, 0.096 mmol), provided as in Example 7, in DMF (5 mL) was stirred while PyBOP® (0.05 g, 0.096 mmol) and aniline (9 mg, 0.096 mmol) were added. The mixture was stirred for an additional 2 minutes and diisopropylethylamine (12.4 mg, 0.096 mmol) was added. The mixture was stirred for 2 hours at room temperature, poured into cold water 0° C. at and extracted with ethyl acetate (4×30 mL). The extracts were combined, dried (MgSO4) and then concentrated. The product was purified from the residue by flash chromatography eluting with 1:2 hexanes/ethyl acetate to provide benzyl 3-methyl-1-[2-hydroxy-1-phenethyl-2-(4-phenylcarbamoyloxazol-2-yl)ethylcarbamoyl]butylcarbamate (30 mg, 0.05 mmol) as a white solid. MS (ESI)) m/z=599 (M+1); 1H NMR (CDCl3): δ 0.8-1.05 (d, J=4 Hz, 6H), 1.35 (m, 1H), δ 1.55 (m, 1H), δ 2.00-2.15 (m, 2H), δ 2.62 (m, 2H), δ 2.80 (m, 2H), δ 3.65 (m, 2H), δ 4.11 (m, 1H1), δ 4.30 (m, 1H), δ 4.45 (m, 1H), δ 4.95 (s, 1H) 5.17 (s, 2H), δ 5.2 (d, J=4 Hz, 1H), δ 6.70 (d, J=5 Hz 1H), δ 7.1-7.45 (m, 15H) 7.7(d, J=4 Hz, 1H), δ 8.19 (s, 1H), δ 8.99 (s, 1H), (C34H38N4O6).

Provenance & Evidence