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21st October 2012 @ 22:26
AEW%2016-1.png

AEW 10-1 (100 mg, 0.43 mmol, 1 equiv.) was dissolved in DCM (5.8 mL), EDCI (99 mg, 0.52 mmol, 1.2 equiv.) and HOBt (6 mg, 0.04 mmol, 0.1 equiv.) were added and the mixture stirred for 20 minutes. Dimethylamine (~5.6 M in absolute ethanol, 0.115 mL, 0.64 mmol, 1.5 equiv.) was added and the reaction mixture stirred at room temperature (9 am). After 5 h, TLC showed spot to spot conversion to another product. The reaction was poured into a saturated aqueous solution of sodium bicarbonate (8 mL), extracted with DCM (3 x 8 mL), washed with brine, dried (MgSO4), filtered and evaporated to give a yellow oil. Crude 1H NMR looked promising. The oil was purified by flash column chromatography over silica, 10-20% EtOAc in DCM to afford a pale yellow semi-solid (53 mg, 0.20 mmol, 47% yield).

TLC, 10% EtOAc in DCM:
IMG_0386.jpg


Crude 1H NMR:

AEW16-1crude.zip
Crude 16-1.pdf


Hazard and Risk Assessment:

As for: EDC Coupling of Pyrrole Carboxylic acid with Hydrazine Hydrate (AEW 14-1), but with dimethylamine in absolute ethanol which is highly flammable, causes burns, is harmful by inhalation and if swallowed and is a lachrymator. Category 2, U and Sl.
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Attached Files
AEW 16-1.png
IMG_0386.jpg
Crude 16-1.pdf
AEW16-1crude.zip
AEW 16-1.png
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