反应详情

To a solution of 2-[{3-[4-(2-hydroxyethyl)piperazin-1-yl]-3-oxopropyl}(4-methoxy-benzenesulfonyl)amino]-3-methylbutyric acid hydrochloride (1.10 grams, 2.17 mmol) in methylene chloride (50 mL) and N,N-dimethylformamide (0.5 mL) were added sequentially O-benzylhydroxylamine hydrochloride (0.41 grams, 2.60 mmol), triethylamine (0.91 mL, 6.5 mmol) and (benzotriazol-1-yloxy)tris-(dimethylamino)-phosphonium hexafluoroborate (1.20 grams, 2.71 mmol). The resulting mixture was stirred for 16 hours at room temperature and then concentrated in vacuo. The residue was taken up in ethyl acetate and washed successively with saturated sodium bicarbonate solution, water and brine. The solution was dried over magnesium sulfate and concentrated to yield an oil which was chromatographed on silica gel eluting with 3% methanol in chloroform to afford N-benzyloxy-2-[{3-[4-(2-hydroxyethyl)piperazin-1-yl]-3-oxopropyl}(4-methoxybenzenesulfonyl)amino]-3-methylbutyramide as a clear oil (0.85 grams, 68%). Conversion to the hydrochloride salt was subsequently carried out using anhydrous hydrochloric acid in cold (0° C.) methylene chloride.

1. concentrationconcentrated in vacuo
2. washwashed successively with saturated sodium bicarbonate solution, water and brine
3. dry with materialThe solution was dried over magnesium sulfate
4. concentrationconcentrated
5. customto yield an oil which
6. customwas chromatographed on silica gel eluting with 3% methanol in chloroform