4-{[(benzyloxy)carbonyl]amino}benzoic acid → HCID 58554730, compound

Participants

Reaction Steps

To a solution of 4-(benzoyloxycarbonylamino)benzoic acid 10 (0.650 g, 2.40 mmol), EDC HCl (0.510 g, 2.65 mmol) and DMAP (0.044 g, 0.36 mmol) in CH2Cl2 (20 mL) was added (S)-1-benzyl 5-(2-hydroxyethyl) 2-(9H-carbazol-9-yl)pentanedioate 23 (0.800 g, 1.85 mmol). After the reaction mixture was refluxed for 6 h, the solution was extracted with CH2Cl2 (100 mL) and water (100 mL). The organic layer was washed with brine (100 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography using CH3OH:CH2Cl2 (1:99) as eluent to afford (S)-1-benzyl 5-(2-(4-(benzyloxycarbonylamino)benzoyloxy)-ethyl) 2-(9H-carbazol-9-yl)pentanedioate 24 (0.80 g, 63%) as a white solid.

Provenance & Evidence