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14th November 2011 @ 06:36
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Coupling of PMY 22-1 and Glycolamide using EDC and DMAP to obtain the N-p-trifluoromethyl-phenyl analogue of TCMDC-123812.

Reaction Scheme

Reaction start time: 1035 15/11/11
EDC.HCl (74 mg, 0.39 mmol, 1.1 equiv.) was stirred in DCM (5 mL) at 0 °C. Triethylamine (0.05 mL, 0.5 mmol, 1.1 equiv.) was added, followed by PMY 22-1 (100 mg, 0.35 mmol, 1 equiv.) and glycolamide (29 mg, 0.51 mmol, 1.1 equiv.). After 24 hours, TLC shows consumption of acid and new products. Water added at 26 hours. Separated and washed with water (2 × 5 mL) and brine then dried (MgSO4) and concentrated under reduced pressure to a pale brown solid (0.14 g). After Chromatography (MeOH/DCM), expected products were not observed by 1H NMR.

Risk and Hazard Assessment:
See: Synthesis of TCMDC-123812 via acid chloride (PMY 10-1)

TLC (10% MeOH/DCM) visualised with vanillin and UV:
TLC 1 hour
TLC 1000 16/11/11

TLC of reactions PMY 23-1, 24-1 and 25-1. Mixed spots with respective acids.

NMR:
1H NMR PMY 25-1-A
1H NMR PMY 25-1-A2
1H NMR PMY 25-1-B


See also:
Synthesis of N-p-tolyl analogue of TCMDC-123812 (PMY 24-1)
Synthesis of N-Phenyl analogue of TCMDC-123812 (PMY 23-1)
Synthesis of TCMDC-123812 via acid chloride (PMY 10-2)
Hydrolysis of Ethyl 2,5-dimethyl-1-phenyl-1H-pyrrole-3-carboxylate (PMY 20-1)
Linked Posts
Attached Files
Reaction Scheme
TLC 1 hour
TLC 1000 16/11/11
1H NMR PMY 25-1-A
1H NMR PMY 25-1-A2
1H NMR PMY 25-1-B