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

To 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.

1. additionwere subsequently added
2. customconsumption of starting material
3. additionThe reaction mixture was diluted with saturated NH4Cl and EtOAc
4. customthe layers separated
5. extractionThe aqueous layer was extracted 2× with EtOAc
6. washthe combined organic extracts were washed with 1 N HCl and brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude product was purified

ORD record

ord-b71a08174352423d9dc2227546fe4c2a

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08530456B2