反应详情

To a solution of 0.75 g (2.09 mmol) of [2-phenyl-4-aminobenzoyl]methionine methyl ester (compound 8) and 0.7 g (2.1 mmol) of (2S,4R)-1-Boc-4-[t-butyldimethylsilyloxy]-pyrrolidin-2-aldehyde, prepared as in Example 171B, in 10 ml of methanol were added 1 ml of acetic acid, followed by 0.2 g (3.1 mmol) of sodium cyanoborohydride. The reaction mixture was stirred overnight. After removal of the solvent, the residue was partitioned with ethyl acetate and 5% sodium bicarbonate, and extracted 3 times with ethyl acetate. The combined organic solution was washed with water and brine, dried over magnesium sulfate, and solvent was removed. The residue was flash-chromatographed on silica gel (2:1 hexanes-ethyl acetate) to yield 261 mg (74%) of {4-[(2S,4R)-1-Boc-4-(t-butyldimetylsilyl)oxypyrrolidin-2-ylmethyl]amino-2-phenylbenzoyl}methionine methyl ester as a white solid: mp 48° C.; [α]25D−15.6 (c=1.03, CHCl3);

1. customAfter removal of the solvent
2. customthe residue was partitioned with ethyl acetate and 5% sodium bicarbonate
3. extractionextracted 3 times with ethyl acetate
4. washThe combined organic solution was washed with water and brine
5. dry with materialdried over magnesium sulfate, and solvent
6. customwas removed
7. customThe residue was flash-chromatographed on silica gel (2:1 hexanes-ethyl acetate)