Diisopropylethylamine → (R)-N-hydroxy-3-phenyl-2-(4-propoxy-benzenesulfonylamino)-propionamide

Participants

Reaction Steps

To 400 mg (˜0.33 mmol) resin from stage 1.1 are added successively dry dichloromethane (2 ml), 4-dimethylaminopyridine (4 mg, 0.033 mmol), 4-propoxy-benzenesulfonyl chloride (309.8 mg, 1.32 mmol) dissolved in dry dichloromethane (1 ml), and N-ethyldiisopropylamine (0.28 ml, 1.64 mmol). After shaking for 15 h at r.t. the suspension is filtered and the resin washed with dichloromethane (3×), alternating with DMA and H2O (2×), 0.2M aqueous citric acid, alternating with DMA and H2O (2×), alternating with 2-propanol and THF (3×), and with dichloromethane (4×). The resin is dried under reduced pressure to provide polymer-bound (R)—N-hydroxy-3-phenyl-2-(4-propoxy-benzenesulfonylamino)-propionamide.

Provenance & Evidence