Benzenepropanoic acid → N-(3-phenylpropionyl)-L-proline benzyl ester

Temperature

0 °C

N,N'-dicyclohexylcarbodiimide (18.77 g) was added to a methylene chloride solution (250 ml) containing L-proline benzylester hydrochloride (20.00 g), triethylamine (11.53 ml), and 3-phenylpropionic acid (13.67 g), and the mixture was stirred at 0° C. for 20 hours. After the precipitated dicyclohexylurea was filtered off, the filtrate was concentrated. The residue was dissolved in ethyl acetate, and the resultant solution was successively washed with 1N hydrochloric acid, saturated sodium hydrogencarbonate, and brine, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to obtain 26.13 g of N-(3-phenylpropionyl)-L-proline benzyl ester.

1. filtrationAfter the precipitated dicyclohexylurea was filtered off
2. concentrationthe filtrate was concentrated
3. dissolutionThe residue was dissolved in ethyl acetate
4. washthe resultant solution was successively washed with 1N hydrochloric acid, saturated sodium hydrogencarbonate, and brine
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated
7. customThe residue was purified by silica gel column chromatography

ORD record

ord-121f845f65934d1f8f50b94995c1b042

Source dataset

uspto-grants-1993_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05204462