Sodium Iodide → HCID 131734844, compound

Participants

Reaction Conditions

Reaction Steps

1-tert-Butyl (S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonylmethoxycarbonyl-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate (18 mg, 0.0233 mmol) was dissolved in dichloromethane (1.8 mL), and bromoethyl acetate (8.2 μL, 0.0700 mmol), N,N-diisopropylethylamine (12.2 μL, 0.0700 mmol), and sodium iodide (10.5 mg, 0.0700 mol) were added. The mixture was stirred at 40° C. for 19 hours and cooled to room temperature, and a saturated aqueous solution of ammonium chloride (15 mL) was then added. After ethyl acetate extraction, the organic layer was dried over anhydrous sodium sulfate. The solvent was then distilled off to obtain 19 mg of crude 1-tert-butyl 4-(1-acetoxy-ethyl) (S)-2-{(E)-(S)-1-[(S)-2-(4-but-2-ynyloxy-phenyl)-1-methoxycarbonylmethoxycarbonyl-ethylcarbamoyl]-10-oxo-heptadec-2-enyl}-2-hydroxy-succinate. The obtained crude product was used in the next reaction without further purification (ESI (LC/MS positive mode) m/z 858 (M+H); Rt 2.82 min.).

Provenance & Evidence