Benzyl Bromide → HCID 70004574, compound

Participants

Reaction Steps

A solution of 346.5 mg (0.5 mmol) (2S,4R)-{[1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carbonyl]-amino}-acetic acid tert-butyl ester in 3 ml DMF was treated at 0° C. with 0.24 ml (2 mmol) benzylbromide and 35 mg (0.8 mmol) 55% NaH, warmed up over night to RT. The reaction was poured into aqueous saturated NH4Cl/EtOAc (3×). The organic phase was washed with aqueous 10% NaCl solution, dried over Na2SO4 and evaporated under reduced pressure. Purification by flash-chromatography on silicagel (Hexane/EtOAc 9:1) gave 277 mg (71%) (2S,4R)-[Benzyl-[1-(naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carbonyl]- amino}-acetic acid tert-butyl ester, MS: 781 (M-H)−.

Provenance & Evidence