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20th August 2012 @ 02:13
Synthesised pure MD 5-1 (0.15 g, 0.5 mmol, 47% yield) which was found to be pure by H1NMR and elemental analysis and has been sent for biological testing.

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Synthesis of OSDD desired synthetic compound, 1-amino-2-methyl-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate.

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Reaction start time: 1:32 PM EST 20/8/12

MD 2-1 (0.24 g, 1 mmol, 1 equiv) and 2-Bromo-2-methylpropionamide (0.32 g, 2 mmol, equiv) were dissolved in a acetonitrile and water mixture (4.2 mL, 95:5). Silver Oxide (0.46 g, 2 mmol, 2 equiv) was added and the reaction was left at room temperature covered in aluminium foil.

At 4:30 PM TLC showed starting product had been consumed and a second TLC showed that starting product had not just turned into a salt with the silver. The reaction was filtered through cellite with methanol and left in the fridge overnight.

The mixture was then concentrated to give the crude product (0.34 g) which included the expected product MD 5-1 by H1NMR . The crude product was then columned (50:50 EtOAc:Hexane)to give the final pure product (0.15 g, 0.5 mmol, 47% yield) which was found to be pure by H1NMR and elemental analysis.

See also:
A direct functionalization of tertiary alkyl bromides with O-, N-, and C-nucleophiles
Hyrdolysis of Ethyl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (MD 2-1)

Risk and Hazard assessment:
MD 5-1 RA
Linked Posts
Attached Files
MD 5-1 Reaction.png
MD 5-1 RA