Pyridine → HCID 131723951, compound

Participants

Reaction Conditions

Reaction Steps

The 3″-amide of L-Cys(Oallyl) was prepared following the general description of Example 5. To this 3″-amide (50 mg) and pyridine (44 μL) in CH2Cl2 (0.25 mL) at −50° C. was added neat (CF3SO2)2O(13 μL) dropwise down the side of the flask to pre-cool it. After the addition was complete, the solution was stirred at −78° C. for 10 min, then allowed to warm to 0° C. in an ice bath. The solution was aged for 7.5 h at 0° C. and L-cysteine ally ester (26 mg) in CH2Cl2 (0.1 mL) was added. The solution was allowed to warm to room temperature and was aged overnight. The solution was poured into saturated NaHCO3(aq), extracted with CH2Cl2 and dried (Na2SO4). The solution was filtered, concentrated under reduced pressure and pure 7,24-bis-O-triethylsilyl protected title compound was obtained following PTLC on silica gel (1×1000 μm plate) using 3/7 acetone/hexanes as eluant. The pure product thus obtained was characterized by 1H NMR.

Provenance & Evidence