Acetyl chloride → (2R)-2-[N-(4-Acetylaminobenzyl)-N-(4-chlorobenzenesulfonyl)amino]-4-methyl-pentanoic acid amide

Participants

Reaction Steps

A solution of the compound of Example 48[(2R)-2-[N-(4-chlorobenzenesulfonyl)-N-(4-aminobenzyl)amino]-4-methyl-pentanoic acid amide (250 mg, 0.60 mmol) and Et3N (120 mg, 1.2 mmol) in CH2Cl2 (20 mL) was treated with acetyl chloride (56 mg, 0.72 mmol). After stirring for 18 h, the reaction was concentrated, chromatographed using silica gel flash chromatography (1% methanol/CH2Cl2) to afford the titled compound (110 mg, 41%). MS (ESI), (M−H)− 422.9; 1H NMR (CDCl3) δ 7.67 (d, 2H, J=8.0), 7.28-7.46 (m, 6H), 7.12 (br s, 1H), 6.24 (br s, 1H), 5.19 (br s, 1H), 4.48 (dd, 2H, J=50, 15), 4.27 (t, 1H, J=7.0), 2.18 (s, 3H), 1.80-2.01 (m, 1H), 1.12-1.32 (m, 2H), 0.75 (d, 3H, J=7.0), 0.67 (d, 3H, J=7.0).

Provenance & Evidence