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24th October 2012 @ 06:25
Conversion of carboxylic acid PMY 59-3 to the primary amide using EDC and ammonium hydroxide as for PMY 60-3.

PMY60-3.png

Reaction Start Time: 17.05 24/10/12
PMY 59-3 (102 mg, 0.34 mmol, 1 equiv.) was stirred in DCM (7 mL, 0.05M). Partial solution. EDC.HCl (85 mg, 0.44 mmol, 1.3 equiv.) and HOBt (approx 4 mg) was added. EDC.HCl dissolves quickly. After 10 mins, clear solution with some needles. After 20 minutes, 28% NH4OH (1 mL) was added and the reaction left to stir. After overnight stirring, saturated NH4Cl(aq) was added. The layers were separated and the aqueous layer extracted with DCM (3 × 10 mL). The combined organic layers were washed with brine, dried (MgSO4) and concentrated to a pale yellow solid (113 mg). 1H NMR shows multiple products, peaks close to SM and PMY 60-3; inconclusive. Purified by chromatography on silica (5% MeOH, 1% NH4OH/DCM) gave slightly yellow solid (84 mg). 1H NMR mainly consistent with PMY 60-3 and impurities. Further chromatography on silica (2-5% MeOH/DCM) gave an early running fraction and 2 other fractions, -A and -B, white solids.

TLC visualised with UV and vanillin
TLC crude MeOH/DCM
TLC column 2

10% MeOH/DCM

TLC crude MeOH/NH4OH/DCM

10% MeOH/1% NH4OH/DCM

NMR:
1H NMR crude
1H NMR column 1


See Also:
Hydrolysis of PMY 58-3 methyl ester (PMY 59-3)
Conversion of oxazole carboxylic acid to primary amide (PMY 60-3)
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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Attached Files
TLC crude MeOH/DCM
TLC crude MeOH/NH4OH/DCM
TLC column 2
1H NMR crude
1H NMR column 1