4-Nitrophenyl chloroformate → HCID 58557070, compound

Participants

Reaction Steps

To a scalemic mixture enriched in (1R,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanol (1.20 g, 2.82 mmol) in pyridine (10 mL) was added DMAP (0.103 g, 0.846 mmol) and 4-nitrophenyl carbonochloridate (0.853 g, 4.23 mmol). The resulting mixture was stirred at ambient temperature for about 1 h. The reaction mixture was purified using silica gel chromatography eluting with 0-30% EtOAc in DCM to give a scalemic mixture enriched in (1R,3R,4S)-3-ethyl-4-(6-tosyl-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentyl 4-nitrophenyl carbonate (0.72 g. 43%): LC/MS (Table 1, Method b) Rt=2.64 min; MS m/z: 591 (M+H)+.

Provenance & Evidence