[C:1]([OH:7])(=O)[CH2:2][CH2:3][CH:4]=[CH2:5].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[C:22]1([C@H:28]([CH2:30][OH:31])[NH2:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[OH:31][CH2:30][C@H:28]([NH:29][C:1](=[O:7])[CH2:2][CH2:3][CH:4]=[CH2:5])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1To a solution of 4-pentenoic acid (2.55 mL, 25.0 mmol) in DMF (312 mL) cooled in an ice/water bath was added HOBt (3.37 g, 25.0 mmol) and EDC (4.79 g, 25.0 mmol) and the resulting solution was stirred for 30 min (R)-(−)-2-phenylglycinol (3.43 g, 25.0 mmol), iPr2NEt (17.8 mL, 100 mmol), and DMAP (0.305 g, 2.50 mmol) were subsequently added and the reaction mixture was stirred 16 h at which point LC-MS analysis indicated complete consumption of starting material. 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 3.5 g of product as a colorless oil in 64% yield. LRMS (M+H)+: 220.1.
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