HCID 86649304, compound → HCID 59627241, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl (1S)-1-(4-bromophenyl)ethyl(3-((S)-tert-butylsulfinylimino)-3-(4-fluorophenyl)propyl)carbamate (200 mg, 0.4 mmol) in anhydrous THF (5 mL) was added 1M allylmagnesium bromide (1.2 mL, 1.2 mmol) at −78° C. The reaction mixture was stirred at −78° C. for 4 h and allowed to warm to rt. After stirring for 2 h at rt, the reaction mixture was quenched with satd aq NH4Cl and extracted with EtOAc (2×). The combined organic phases were dried, filtered and concentrated to give a residue, which was purified by TLC to provide methyl (S)-1-(4-bromophenyl)ethyl((S)-3-((S)-1,1-dimethylethylsulfinamido)-3-(4-fluorophenyl)hex-5-enyl)carbamate (96 mg, 45%). 1H NMR (CD3OD): 1.28 (m, 9H), 1.48 (m, 3H), 2.10 (m, 1H), 2.30 (m, 1H), 2.72 (m, 4H), 3.66 (m, 3H), 5.08 (m, 2H), 5.40 (m, 2H), 7.10 (m, 4H), 7.32 (m, 2H), 7.50 (m, 2H).

Provenance & Evidence