Ethyl chloroformate → 3-(4-Benzyloxy-3-methoxy-phenyl)-propionamide

Temperature

-15 °C

To a stirred solution of 3-(4-benzyloxy-3-methoxy-phenyl)-propionic acid (8.38 g, 29.30 mmol) in dry THF (110 ml), under nitrogen, was added TEA (4.5 ml, 32.33 mmol), and the resulting mixture was cooled to −10° C. before ethyl chloroformate (3.1 ml, 32.53 mmol) was added dropwise. After stirring at −10° C. (20 min), ammonium hydroxide (25% in water, 65 ml) in THF (65 ml) was added and the mixture was stirred at −15° C. for 30 min and then at RT for 1.5 h. The reaction mixture was concentrated in vacuo, extracted three times with CH2Cl2 and the combined organic extracts were washed with saturated aqueous NaHCO3 and brine. The organic phase was dried over anhydrous MgSO4, filtered and concentrated to give the title compound (8.40 g, 29.30 mmol, 100%) as a colorless solid. No further purification of the crude amide was necessary.

1. additionwas added dropwise
2. additionwas added
3. waitat RT for 1.5 h
4. concentrationThe reaction mixture was concentrated in vacuo
5. extractionextracted three times with CH2Cl2
6. washthe combined organic extracts were washed with saturated aqueous NaHCO3 and brine
7. dry with materialThe organic phase was dried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-4b87c93c90e7498ea6fef75bd7789d22

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07192950B2