Trifluoroacetic acid → HCID 118512009, compound

Participants

Reaction Steps

To a solution of (R)-2-(1-amino-3-(benzyloxy)propyl)-1-tosyl-1H-pyrrole-3-carboxylic acid compound with TFA (1:1) (504d, 5.43 g, 10.01 mmol) and DIEA (5.22 mL, 30.0 mmol) in EtOAc (50 mL) was added 1-propanephosphonic acid cyclic anhydride (50 wt. % in EtOAc, 5.96 mL, 10.01 mmol) dropwise via syringe. All solids dissolved to give a light brown solution. After 1 h, the reaction was partitioned between sat'd NaHCO3 and EtOAc. The organic layer was washed with sat'd NaHCO3 once, sat'd NaCl once, and the organics were dried over anhydrous MgSO4, filtered, and concentrated in vacuo to give (R)-6-(2-(benzyloxy)ethyl)-1-tosyl-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (724e) (3.51 g, 8.55 mmol, 85% yield) as a light brown foam. m/z (ESI, +ve) 411.1 (M+Na)+.

Provenance & Evidence