Potassium Carbonate → prop-2-enyl (6S,6aS)-3-[3-[[(6S,6aS)-6-[tert-butyl(dimethyl)silyl]oxy-2-methoxy-5-[[4-[[(2R)-2-[[(2R)-3-methyl-2-(prop-2-enoxycarbonylamino)butanoyl]amino]propanoyl]amino]phenyl]methoxycarbonyl]-11-oxo-8-[(E)-prop-1-enyl]-6a,7-dihydro-6H-pyrrolo[2,1-c][1,4]benzodiazepin-3-yl]oxy]propoxy]-6-[tert-butyl(dimethyl)silyl]oxy-2-methoxy-11-oxo-8-[(E)-prop-1-enyl]-6a,7-dihydro-6H-pyrrolo[2,1-c][1,4]benzodiazepine-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

Potassium carbonate (0.030 g, 0.21 mmol, 1.0 eq) was added to a solution of the phenol 18 (0.175 g, 0.21 mmol, 1.0 eq) and the iodo linker 49 (0.214 g, 0.32 mmol, 1.5 eq) in acetone (10 mL). The reaction mixture was heated under a nitrogen atmosphere at 75° C. in a sealed flask for 17 hours. The reaction mixture was concentrated to dryness under reduced pressure and purified by flash chromatography (silica gel, 2/98 v/v methanol/DCM to 5/95 v/v methanol/DCM) to afford the product as a pale yellow solid (0.100 g, 35%). LC/MS (4.293 min (ES+)), m/z: 1359.13 [M]+.

Provenance & Evidence