反应详情

tert-butyl N-((1S,2R)-1-benzyl-3-(cyclohexyloxy)[(4-methoxyphenyl)sulfonyl]amino-2-hydroxypropyl)carbamate (0.09 mmol, 50 mg) was dissolved in a 1:1 solution of CH2Cl2/TFA (1 mL) and allowed to stir at room temperature for 1 hour. The solution was then extracted into ethyl acetate, washed with saturated sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated to a clear oil. The resulting oil was then dissolved in THF (1 mL) and combined with 2,5-dioxo-1-pyrrolidinyl [(3S)tetrahydro-3-furanyl] carbonate (0.05 mmol, 13 mg) DIEA (0.08 mmol, 14 μL) and allowed to stir for 15 hours. The reaction was neutralized by the addition of acetic acid and partitioned between water and ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and brine, and dried over magnesium sulfate. The crude product was concentrated to a white solid and purified by silica gel chromatography (1:1 hexanes/ethyl acetate), providing 19 mg (37%) of a white solid. H1-NMR (CDCl3): δ 7.70 (2H,d), 7.29-7.17 (6H,m), 6.97 (2H,d), 5.1 (1H,s), 4.76 (1H,d), 4.17 (1H,m), 3.86 (3H,s), 3.87-3.70 (6H,m), 3.68-3.60 (1H,m), 3.06 (1H,bs), 2.89 (2H,m), 2.02 (3H,m), 1.89 (1H,m), 1.71 (2H,m), 1.28-1.08 (6H,m); MS (ESI): M+Na=585.

1. extractionThe solution was then extracted into ethyl acetate
2. washwashed with saturated sodium bicarbonate solution and brine
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated to a clear oil
5. dissolutionThe resulting oil was then dissolved in THF (1 mL)
6. stirringto stir for 15 hours
7. custompartitioned between water and ethyl acetate
8. washThe organic layer was washed with saturated sodium bicarbonate and brine
9. dry with materialdried over magnesium sulfate
10. concentrationThe crude product was concentrated to a white solid
11. custompurified by silica gel chromatography (1:1 hexanes/ethyl acetate)