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1st August 2012 @ 01:54
Decomposition of starting material into multiple unknown products.

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Conversion of PMY 59-1 oxazole carboxylic acid to primary amide via reaction of the acid chloride with ammonia.

PMY60-1.png

Reaction Start Time: 10.55 01/08/12
PMY 59-1 (62 mg, 0.21 mmol, 1 equiv.) was stirred in DCM (5 mL). Oxalyl chloride (53 μL, 0.62 mmol, 3 equiv.) was added. Reaction is a partial solution. DMF (1 drop) was added, bubbling is observed and the reaction becomes a solution. After 1 hour, the reaction was concentrated under reduced pressure. The residue was dissolved in THF (5 mL). Ammonia gas was bubbled through the solution for 30 minutes. A precipitate formed and the reaction was a hazy suspension. After a further hour, TLC shows absence of starting material and numerous product spots. The reaction was concentrated under reduced pressure to a yellow solid.

10.10 02/08/12 The residue was purified by chromatography on silica (5-50% acetone/hexane) 4 fractions obtained.

PMY 60-1-A (approx 10 mg), not consistent with product by 1H NMR.
PMY 60-1-B (approx 10 mg), not consistent with product by 1H NMR.
PMY 60-1-C (approx 10 mg), not consistent with product by 1H NMR.
PMY 60-1-D (approx 10 mg), not consistent with product by 1H NMR.

TLC (50% acetone/hexane) visualised with UV and vanillin:
TLC


LC/MS:
LCMS, 60-1-B


NMR:
1H NMR PMY 60-1-D actual
1H NMR PMY 60-1-C actual
1H NMR PMY 60-1-B
1H NMR PMY 60-1-A


See also:
Hydrolysis of PMY 58-2 methyl ester (PMY 59-1)
Synthesis of TCMDC-123812 via acid chloride (PMY 10-2)
Synthesis of pyrrole amide (PMY 42-1)

Risk and Hazard Assessment:
New form:
RA


Previous risk assessments:
Synthesis of TCMDC-123812 via acid chloride (PMY 10-2)
Synthesis of pyrrole amide (PMY 42-1)
Linked Posts
Attached Files
RA
Scheme
TLC
LCMS, 60-1-B
1H NMR PMY 60-1-A
1H NMR PMY 60-1-B
1H NMR PMY 60-1-D actual
1H NMR PMY 60-1-C actual