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16th October 2012 @ 04:21
1H NMR and LC/MS hint toward product. Not quite clean enough.

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Conversion of recovered carboxylic acid PMY 60-2 to the primary amide using EDC and ammonium hydroxide.

PMY60-3.png

Reaction Start Time: 14.10 16/10/12
PMY 60-2 (15 mg, 0.05 mmol, 1 equiv.) was stirred in DCM (5 mL) under nitrogen at room temperature. Reaction was a hazy solution. EDC.HCl(12 mg, 0.06 mmol, 1.2 equiv.) and HOBt (approx 1 mg) was added and the reaction stirred. After 20 minutes, 28% ammonium hydroxide solution (1 mL) was added. After 3 hours, LC/MS shows conversion to amide.

LC/MS:
Crude LC/MS


NMR:
1H NMR crude


See Also:
EDC Coupling of Pyrrole Carboxylic acid with Hydrazine Hydrate (AEW 14-2)
Conversion of PMY 59-2-B oxazole carboxylic acid to primary amide (PMY 60-2)
Synthesis of N-p-trifluoromethyl-phenyl analogue of TCMDC-123812 (PMY 25-1)

Risk and Hazard Assessment:
As for: Synthesis of N-Phenyl analogue of TCMDC-123812 (PMY 23-1)
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Scheme
Crude LC/MS
1H NMR crude