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13th June 2013 @ 01:04

Repeated to collect data for paper - see original experiment Resynthesis of N-(2-amino-2-oxoethyl)-1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxamide, OSM-S-19 (AEW 59-1) for failed attempt

Procedure:

AEW 10-2 (100 mg, 0.43 mmol, 1 equiv.) was dissolved in CH2Cl2 (4.3 mL) under Argon. 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. Glycinamide hydrochloride (52 mg, 0.47 mmol, 1.1 equiv.) was stirred in a separate flask in THF (0.22 mL) with DIPEA (66 mg, 0.09 mL, 0.51 mmol, 1.2 equiv.) and then transferred to the reaction mixture and stirred at room temperature overnight.

The reaction mixture was diluted in CH2Cland washed with a saturated aqueous solution of sodium hydrogen carbonate. Aqueous layers were extracted with CH2Cl(x 2) and then combined organic layers washed with brine, dried (MgSO4), filtered and evaporated to yield a crude yellow oil. 

The oil was purified by flash column chromatography over silica (0-20% MeOH in CH2Cl2) to give a yellow oil with some crystals within. MeOH (1.5 mL) was added and the mixture cooled to 0 and sonicated and then left in an ice bath for 30 mins. The off white crystals were filtered and washed with ice cold methanol to yield the desired product + impurities (23 mg, 0.08, 18 % yield).

Data:

 

AEW 59-2 cryst proton.pdf
AEW 59-2 crude.zip
AEW 59-2 cryst.zip
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AEW 59-1.png
AEW 59-2 cryst proton.pdf
AEW 59-2 crude.zip
AEW 59-2 cryst.zip