反应详情

Method A (transthioesterification). Phosphinothiol 20 (500 mg, 2.2 mmol) was dissolved in dry TBF (5 mL). The solution was deoxygenated by bubbling Ar(g) for 0.5 h. To this solution was added NaH (51.6 mg, 2.2 mmol). The mixture formed a slurry to which was added DMF (2 mL0 to dissolve any precipitate. The N-methylmercaptoacetamide (NMA) thioester of N-acetylphenylalanine (63 mg, 0.22 mmol) was added, and the reaction mixture was stirred for 8 h. Unreacted Phosphinothiol 20 was removed by adding Merrifield resin (1.5 g, 1.26 mmol/g), stirring for 6 h, and removing the resin by filtration. The residue was purified by flash chromatography (silica gel, 50% ethyl acetate in hexanes). AcPheSCH2PPh2 was isolated as a white solid in 92% yield.

1. customThe solution was deoxygenated
2. customby bubbling Ar(g) for 0.5 h
3. customThe mixture formed a slurry to which
4. dissolutionto dissolve any precipitate
5. customUnreacted Phosphinothiol 20 was removed
6. additionby adding Merrifield resin (1.5 g, 1.26 mmol/g)
7. stirringstirring for 6 h
8. customremoving the resin
9. filtrationby filtration
10. customThe residue was purified by flash chromatography (silica gel, 50% ethyl acetate in hexanes)