Allyl bromide → HCID 70003054, compound

Participants

Reaction Steps

A solution of 346 mg (0.5 mmol) (2S,4R)-{[1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carbonyl]-amino}-acetic acid tert-butyl ester in 10 ml THF at −78° C. was treated with 1.1 ml (1M in THF, 1.1 mmol) Lithium bis(trimethlsilyl)amide solution (LiHMDS). 0.127 ml (1.5 mmol) Allylbromide was added after 30 min and the reaction was warmed up to RT over night. The reaction was partitioned between aqueous 10% KHSO4/EtOAc (4×), the organic phases were washed with aqueous 10% NaCl, dried over Na2SO4 and evaporated. Purification by flash-chromatography on silicagel (Hexane/EtOAc 2:1) and precipitation with Et2O/pentane gave 76 mg (21%) (2RS)-2-{(2S,4R)-[1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carbonyl]-amino}-pent-4-enoic acid tert-butyl ester, MS: 733 (MH+).

Provenance & Evidence