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10th January 2012 @ 03:50
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Synthesis of the amide analogue of TCMDC-123812 by coupling of glycinamide and acid PMY 8-3 at 50 °C.

Reaction Scheme

Reaction start time: 15.25 10/01/12
Glycinamide.HCl (78 mg, 0.71 mmol, 1.1 equiv.) and PMY 8-3 (150 mg, 0.63 mmol, 1 equiv.) were dissolved in DMF (3 mL) and pyridine (0.3 mL, 3.9 mmol, 6 equiv.) was added. Glycinamide appears to have dissolved (dark solution). The mixture was heated to 50 °C. 15.56 T3P 50% in EtOAc (0.80 mL, 1.26 mmol, 2 equiv.) was added. After 20 hours, TLC shows starting material still remains. After 44 hours, TLC shows SM still. Water (30 mL) added. EtOAc (20 mL) added. Emulsion, pH 4. 10% NaHCO3 (approx 10 mL) added. Separated. Aqueous extracted with EtOAc (2 × 20 mL). Combined extracts washed with water, brine, dried (MgSO4) and concentrated under reduced pressure to a brown solid (approx 130 mg). 1H NMR shows small conversion to a number of products.

TLC (10% MeOH/DCM) visualised with UV and vanillin:
TLC 1 hour
TLC 20 hours
TLC 44 hours

DMF interfering with Rf. TLC 20 hrs: Left plate, neat rxn. Middle plate, TLC of micro work-up (water, EtOAc partition). Right plate, 5% MeOH/DCM, micro work-up.

NMR:
1H NMR crude


See also:
Coupling of pyrrole carboxylic acid PMY 8-3 and glycinamide (PMY 31-1)

Risk and Hazard Assessment:
See: Synthesis of TCMDC-123812 using T3P (PMY 10-4)
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Scheme
TLC 1 hour
TLC 20 hours
TLC 44 hours
1H NMR crude