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18th May 2012 @ 04:08
MNR14-3%20scheme.png

KAB6-1 (0.29 g, 0.73 mmol) in toluene (4 mL) was treated with methanesulfonic acid (0.05 mL, 0.73 mmol) and the reaction was stirred at room temperature for 5 hours by which time TLC had shown complete consumption of SM. The reaction was neutralised with sat. sodium hydrogen carbonate solution, the organic fraction extracted and the aqueous fraction was washed with EtOAc (10 mL x 3). The organic layers were combined, dried, filtered and concentrated to give a dark orange oil.

TLC after 5 hours in 100% EtOAc
MNR14-3 5 hours


Crude - 0.277 g

Column 30-100% EtOAc

Fracs 36-65 as MNR14-3-INT 0.028 g

MNR14-3-INT.png


Other frac - 0.182 g - messy NMR's

As expected, no fully PS cyclised product isolated. Yield of the intermediate enediamide is low, perhaps to due the delay between running the reaction and running the column or may this is just a messy reaction as it doesn't run cleanly to the desired product.
Attached Files
MNR14-3 5 hours
MNR14-3 scheme.png
mnr14-3-int_1H.pdf
MNR14-3-INT.png