TCMDC_ArylPyrrole

 

Product obtained in 64% yield.

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Coupling of hippuric acid and 4-aminoantipyrine using T3P to obtain the glycine benzamide.



Reaction start time: 16.00 11/01/12
Hippuric acid PMY 26-1 (500 mg, 2.79 mmol, 1 equiv.)and 4-aminoantipyrine (623 mg, 3.07 mmol, 1.1 equiv.) were dissolved in DMF (2.5 mL) and pyridine (1.30 mL, 16.14 mmol, 5.78 equiv.). The mixture was cooled in an ice/bath and T3P (50 wt.% in EtOAc, 3.1 mL, 4.9 mmol, 1.74 equiv.) was added. The mixture was allowed to warm to room temperature and the mixture overnight. After 21 hours, TLC shows reaction complete. Water added (10 mL). Precipitate forms and the reaction sets solid. Filtered and washed with water and a small amount of EtOAc. Dried under vacuum, white powder PMY 27-2 (655 mg, 64% of theory). NMR consistent with PMY 27-1

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

Mini-work up:Drop of reaction mixture quenched with water and partitioned with EtOAc.

NMR:


Risk and Hazard Assessment:
As for, Synthesis of TCMDC-123812 using T3P (PMY 10-4)

See also:
Hydrolysis of benzoyl protected glycinamide PMY 27-1 (PMY 28-2)