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15th November 2011 @ 03:39
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Coupling of acid PMY 8-3 and 4-aminoantipyrine for a analogue of TCMDC-123794 that does not contain the ester linker. Using EDC as coupling reagent.

Reaction Scheme

Reaction start time: 1500 15/11/11
EDC.HCl (181 mg, 0.94 mmol, 1.1 equiv.) was stirred in DCM (8 mL) at 0 °C. Triethylamine (0.13 mL, 0.94 mmol, 1.1 equiv.) was added, followed by PMY 8-3 (200 mg, 0.86 mmol, 1 equiv.) and 4-aminoantipyrine (192 mg, 0.94 mmol, 1.1 equiv.). After 19 hours, TLC shows new product. After a total of 22 hours, water added. 21/11/11 Diluted with further DCM (10 mL) and separated. The organic layer was washed with water (2 × 10 mL) and brine, then dried (MgSO4) and concentrated under reduced pressure to a brown oil. Purified by chromatography (0-3% then 10% MeOH/DCM). Not consistent with expected product by 1H NMR.

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


NMR:
1H NMR


Risk and Hazard Assessment:
See Synthesis of TCMDC-123794 Side-chain (PMY 5-1)
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Attached Files
Reaction Scheme
TLC 1000 16/11/11
1H NMR