All Notebooks | Help | Support | About
This is a previous version of this entry. To view the latest click here. or to view all revisions click here.
5th August 2013 @ 02:29

Coupling of Boc-protected glycine and 4-aminoantipyrine using T3P. Repeat of PMY 29-2. AEW63-1 (Resynthesis of tert-butyl (2-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)amino)-2-oxoethyl)carbamate, OSM-S-17 (AEW 63-1)) didn't proceed as well as Paul Ylioja's reaction.

Reaction Scheme

Boc-Gly-OH (500 mg, 2.85 mmol, 1 equiv.) and 4-aminoantipyrine (638 mg, 3.14 mmol, 1.1 equiv.) were dissolved in DMF (2.5 mL) and pyridine (1.30 mL, 16.14 mmol, 5.65 equiv.). The mixture was cooled in an ice/bath and T3P (50 wt.% in EtOAc, 3.1 mL, 4.9 mmol, 1.7 equiv.) was added. The mixture was allowed to warm to room temperature and the mixture overnight. 


TLC (10% MeOH/DCM):

Mini-work up:Drop of reaction mixture quenched with water and partitioned with EtOAc. Potential for SM to have remained in aqueous.


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

See also:
Coupling of Boc-Gly-OH and 4-aminoantipyrine (PMY 29-1)
Hydrolysis of benzoyl protected glycinamide PMY 27-1 (PMY 28-2)
Hydrolysis of benzoyl protected glycinamide PMY 27-1 (PMY 28-1)
Coupling of hippuric acid and 4-aminoantipyrine using T3P (PMY 27-1)