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13th June 2013 @ 01:22

Repeat of Coupling of acid PMY 8-3 and 4-aminoantipyrine using T3P for a linker-less analogue of TCMDC-123794 (PMY 12-5) to collect data for the paper. Using EDCI and HOBt in attempt to enhance yield.

Procedure:

AEW 10-2 (100 mg, 0.43 mmol, 1 equiv.) was dissolved in CH2Cl2 (4.3 mL). EDC (100 mg, 0.51 mmol, 1.2 equiv.) and HOBt (6 mg, 0.04 mmol. 0.1 equiv.) were added and the yellow solution stirred at room temperature for 15 minutes under Argon. 4-Aminoantipyrine (96 mg, 0.47 mmol, 1.1 equiv.) was added and the reaction mixture stirred at rt. New product spots by TLC after 2 hours but still SM. Reaction mixture stirred o/n. Still SM. Reaction quenched by addition of a saturated aqueous soln of NaHCO3extracted into CH2Cl2, washed with water, brine, dried over MgSO4, filtered and evaporated to give an orange oil. Crude proton NMR looks pretty messy. Purification by flash column chromatography over silica (1 to 10% MeOH in DCM) gave the desired product as an orange oil - still not pure. Repurified with a slower gradient. Desired product not isolated cleanly - needs to be repeated.

Data:

AEW 62-1 (10% MeOH in DCM).jpg
 
AEW 62-1 col first spot.pdf
AEW 62-1 crude.zip
AEW 62-1 ck.zip

Hazard and Risk Assessment:


See Coupling of acid PMY 8-3 and 4-aminoantipyrine using T3P for a linker-less analogue of TCMDC-123794 (PMY 12-5) and

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Attached Files
AEW 62-1 scheme.png
AEW 62-1 col first spot.pdf
AEW 62-1 (10% MeOH in DCM).jpg
AEW 62-1 crude.zip
AEW 62-1 ck.zip