2,4,6-Triisopropylbenzenesulfonyl azide → HCID 53941532, compound

Participants

Reaction Steps

A solution of 3-(3(S)-(3,4-dichlorophenyl)-1-oxo-5-hexenyl)-4(S)-benzyl-2-oxazolidinone (190 mg, 0.45 mmol; prepared from 3-(R)-(3,4-dichlorophenyl)-hex-4-enoic acid (from Step B above) and 4(S)-benzyl-2-oxazolidinone according to the procedure of Evans, D. A.; et. al. J. Am. Chem. Soc. 1990, 112, 4011-4030) in THF (2.5 mL) was added to a solution of KHMDS (1.0 mL of 0.5M in PhCH3, 0.50 mmol), and THF (1.5 mL) at -78° C. The reaction was maintained at -78° C. for 30 min whereupon a solution of trisyl azide (177 mg, 0.57 mmol) and THF (1.5 mL) was added. The mixture was stirred for 2 min and HOAc (0.13 mL, 4.6 mmoL) was added. The reaction mixture was stirred 1 h in a 30° C. water bath, whereupon it was diluted with H2O (50 mL) and extracted with CH2Cl2 (3×30 mL). The combined organic extracts were washed with sat. aq. NaHCO3, brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel 60, 15-25% EtOAc/hexanes) to afford the title compound (169 mg, 81%) as a colorless oil.

Provenance & Evidence