Reaction #69353

Reaction equation

EDC

(S)-2-(2-tert-butoxy-2-oxoethyl)pent-4-enoic acid

(R)-N-(2-hydroxy-1-phenylethyl)pent-4-enamide

iPr2NEt

→

desired product

(S)-4-tert-butyl 1-((R)-2-pent-4-enamido-2-phenylethyl) 2-allylsuccinate

Solvents

DMF

Conditions

Workup

1. 1
   workup.ADDITIONwere subsequently added

Procedure

To a solution of (S)-2-(2-tert-butoxy-2-oxoethyl)pent-4-enoic acid (684 mg, 3.19 mmol) in DMF (25 mL) cooled in an ice/water bath was added EDC (612 mg, 3.19 mmol) and the resulting solution was stirred for 30 min. (R)-N-(2-hydroxy-1-phenylethyl)pent-4-enamide (700 mg, 3.19 mmol), iPr2NEt (1.77 mL, 9.58 mmol), and DMAP (39.0 mg, 0.319 mmol) were subsequently added and the reaction mixture was stirred 16 h at which point LC-MS analysis indicated the presence of both starting material and desired product. The reaction mixture was diluted with saturated NH4Cl and EtOAc and the layers separated. The aqueous layer was extracted 2× with EtOAc and the combined organic extracts were washed with 1 N HCl and brine, dried over Na2SO4, filtered, and concentrated. The crude product was purified using silica gel chromatography (MeOH/CH2Cl2 gradient) to yield 340 mg of product as a colorless oil in 26% yield. LRMS (M+Na)+: 438.4.

Source