Diisopropylethylamine → Phenylmethyl (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoyl)-3-({[4-(2-pyridinyl)-2-pyrimidinyl]amino}carbonyl)-1-pyrazolidinecarboxylate

Participants

Reaction Steps

To a solution of (3S)-2-((2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoyl)-1-{[(phenylmethyl)oxy]carbonyl}-3-pyrazolidinecarboxylic acid (800 mg, 1.5 mmol) in THF (10 mL) under N2 was added 2,4,6-trichlorobenzoyl chloride (477 mg, 2 mmol) and DIPEA (1.3 mL, 7.5 mmol). The mixture was stirred at rt for 2 h. THF was removed under vacuum and toluene (10 mL) was added. To this mixture was added 4-(2-pyridinyl)-2-pyrimidinamine (337 mg, 2 mmol) and DMAP (37 mg, 0.3 mmol). After being stirred at rt overnight, the mixture was diluted with EtOAc (50 mL) and washed with 5% citric acid and sat. NaHCO3. The organic solution was dried (Na2SO4) and concentrated. The residue was purified by flash column chromatography to provide the title compound (400 mg, 39%).

Provenance & Evidence