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9th August 2012 @ 05:40
Repeat of MNR41-14 but leaving out the molecular sieves as they could be slightly acidic.

MNR41-4%20scheme.png
mnr41-14%20table.PNG

To a solution of MNR42-1 (0.1 g, 0.32 mmol) in HPLC grade acetonitrile (10 mL) and under argon at 0 °C, was added was added acetyl chloride (0.041 mL, 0.57 mmol), 2,6-lutidine (0.052 mL, 0.48 mmol, fresh out of a new bottle) and PZQ (0.01 g, 0.03 mmol). The reaction was then shaken at room temperature (19 °C) for 1 hour.

After 75 minutes a sample was taken for mini workup and LCMS. The reaction was left to shake.

Work Up

The mixture was washed with EtOAc (20 mL). The filtrate was washed with saturated sodium bicarbonate solution (25 mL). The aqueous layer was extracted with ethyl acetate (3 × 30 mL). The organic fractions were combined, dried over MgSO4, filtered and concentrated under reduced pressure to yield a yellow solid (0.157 g)

The crude was then taken up in IPA (3 ml) in an attempt to crystallise the product overnight. Crystals washed with IPA in the morning.

0.089 g

LCMS

mnr41-15_90mins.pdf


NMR

mnr41-15.pdf


NMR showed clean product

LCMS after 90 mins shows significant product.

Total recovered after 1 recrystallisation - 0.089 g, 0.25 mmol, 78%.
Attached Files
mnr41-15_90mins.pdf
mnr41-15.pdf