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14th November 2011 @ 06:28

Coupling of PMY 20-1 and Glycolamide using EDC and DMAP to obtain the N-phenyl analogue of TCMDC-123812.

Reaction Scheme

Reaction start time: 1035 15/11/11
EDC.HCl (98 mg, 0.51 mmol, 1.1 equiv.) was stirred in DCM (5 mL) at 0 °C. Triethylamine (0.07 mL, 0.51 mmol, 1.1. equiv.) was added, followed by PMY 20-1 (100 mg, 0.46 mmol, 1 equiv.) and glycolamide (38 mg, 0.51 mmol, 1.1 equiv.). After 24 hours, TLC shows consumption of acid and new products. Water added at 26 hours. Reaction left for another 24 hours. Separated and washed with water (2 × 5 mL) and brine then dried (MgSO4) and concentrated under reduced pressure to a brown oil (0.22 g). Purified by chromatography (0,0.25,0.5,1,1.5% MeOH/DCM) to obtain 23-1-A (early product "anhydride", yellow oil (5 mg) and 23-1-B, consistent with expected product by 1H NMR, brown oil (4 mg). really poor mass balance going on here.

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.

1H NMR PMY 23-1-A
1H NMR PMY 23-1-B

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

See also:
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
1H NMR PMY 24-1-A
1H NMR PMY 23-1-B
1H NMR PMY 23-1-A