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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

Procedure:
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 stirred overnight. No SM present.

Data:

TLC (10% MeOH/DCM):

AEW 72-1.jpg

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

NMR:

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)

InChI=1S/C18H24N4O4/c1-12-15(20-14(23)11-19-17(25)26-18(2,3)4)16(24)22(21(12)5)13-9-7-6-8-10-13/h6-10H,11H2,1-5H3,(H,19,25)(H,20,23)

Attached Files
AEW 72-1.jpg