N-Hydroxyphthalimide → 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-3-phenyl-propionic acid benzyl ester

Participants

Reaction Conditions

Reaction Steps

To a mixture of compound from Step 6a (7.00 g, 27.2 mmol), N-hydroxyphthalimide (5.35 g, 32.80 mmol) and PPh3 (9.26 g, 35.30 mmol) in CH2Cl2 (55 mL) was added diisopropyl azodicarboxylate (6.86 mL, 35.38 mmol) during 10 minutes period at −20° C. The resulting mixture was stirred at −20° C. for 2 hours. The solvent was removed under reduced pressure. The residue was purified by flash chromatography (silica gel, CH2Cl2/hexane=1/2) to afford 10.65 g (99%) of the title compound.

Provenance & Evidence