Methyl iodide → HCID 69231382, compound

Temperature

0 °C

To a solution of 3-[5-benzyloxy-2-(isopropoxycarbonylamino-methyl)-phenyl]-propionic acid tert-butyl ester (6.3 g, 0.015 mol) in DMF (100 mL) was added NaH (29.4 mmol, 60% oil dispersion). The reaction mixture was stirred at 0° C. for 15 min, treated with methyl iodide (4.18 g, 29.4 mmol), and stirred overnight under N2 at ambient temperature. The mixture was concentrated and triturated with hexanes (200 mL). The residue was diluted with EtOAc (200 mL), and the solution was washed with water (200 mL) and brine (200 mL), dried (Na2SO4), and concentrated to a yellow oil (5.2 g). The material was dissolved in EtOAc (100 mL), and 5% Pd/C (0.725 g) was added. The reaction mixture was shaken under a hydrogen atmosphere in a Parr apparatus at 60 psi overnight at 40° C. The mixture was filtered and concentrated to give the title compound (2.1 g). MS [ES] m/z 352 (M+H)+.

1. stirringstirred overnight under N2 at ambient temperature
2. concentrationThe mixture was concentrated
3. customtriturated with hexanes (200 mL)
4. additionThe residue was diluted with EtOAc (200 mL)
5. washthe solution was washed with water (200 mL) and brine (200 mL)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated to a yellow oil (5.2 g)
8. dissolutionThe material was dissolved in EtOAc (100 mL)
9. addition5% Pd/C (0.725 g) was added
10. stirringThe reaction mixture was shaken under a hydrogen atmosphere in a Parr apparatus at 60 psi overnight at 40° C
11. filtrationThe mixture was filtered
12. concentrationconcentrated

ORD record

ord-9027606e384a4c98b11a52ab38b86ed2

Source dataset

uspto-grants-2007_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07282501B2