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6th August 2013 @ 07:02

See also: Deprotection of Boc-Gly-4-aminoantipyrine (PMY 30-3), no TFA used at outset as PMY found 4M HCl to be more effective.

Procedure:

Crude AEW 72-1 (~555 mg, ~1.54 mmol) was dissolved in THF (6 mL). Yellow solution. HCl (4M in dioxane, 3 mL, 12 mmol) was added dropwise - reaction mixture turned red - and left to stir at room temperature overnight.

 

Aqueous work up following netralisation of reaction mixture with 2 M NaOH. Partiioned between EtOAC and layers separated. Aqueous washed with EtOAc then combined organic washed with water, brine and dried (MgSO4), filtered and evaporated.

NMR didn't show desired product.

 

Data:

TLC (10% MeOH in CH2Cl2) after 19 hours

 

Hazard and Risk Assessment:

See: Deprotection of Boc-Gly-4-aminoantipyrine (PMY 30-3)

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Attached Files
AEW 64-2 cdcl3.zip
AEW 64-2 rerun.zip