Dicyclohexylcarbodiimide → 4-Carbamoylphenyl 2-(2-methoxynaphthalen-6-yl)propanoate

Temperature

0 °C

To the solution of 1 (naproxen, 4 g, 17.4 mmol) in 80 mL of dimethylformamide, hydroxybenzotriazole (2.59 g, 19.14 mmol) and DCC (2.59 g, 19.14 mmol) were added with stirring at 0° C. for 1 h. To the reaction mixture 4-hydroxybenzamide (4, 3.58 g, 26.1 mmol) was added and stirred for 1 h at 0° C. and 2 h at room temperature. After filtration, the filtrate was evaporated under reduced pressure to remove the solvent. The oily residue thus obtained was dissolved in ethyl acetate; the organic layer was washed with brine, with NaHCO3 5%, with citric acid 10% and than dried on anhydrous MgSO4, filtered and the solvent evaporated. The crude product 5 was loaded on a silica gel open column and eluted with CH2Cl2/MeOH (9.5/0.5), from which 4-carbamoylphenyl 2-(2-methoxynaphthalen-6-yl)-propanoate (5) was obtained (1.91 g, 32% yield).

1. stirringstirred for 1 h at 0° C. and 2 h at room temperature
2. filtrationAfter filtration
3. customthe filtrate was evaporated under reduced pressure
4. customto remove the solvent
5. customThe oily residue thus obtained
6. washthe organic layer was washed with brine, with NaHCO3 5%, with citric acid 10%
7. dry with materialthan dried on anhydrous MgSO4
8. filtrationfiltered
9. customthe solvent evaporated
10. washeluted with CH2Cl2/MeOH (9.5/0.5), from which 4-carbamoylphenyl 2-(2-methoxynaphthalen-6-yl)-propanoate (5)
11. customwas obtained (1.91 g, 32% yield)

ORD record

ord-c11d4f78d0c14be3a589fbedfb45332e

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07741359B2