Methyl iodide → HCID 59072630, compound

To a suspension of N-[[1-(2-methoxyethyl)cyclopentyl]carbonyl]-4-nitro-L-phenylalanine methyl ester (2.73 mmol, 1.03 g) and silver oxide (10.9 mmol, 2.53 g) in DMF (25 mL) was added methyl iodide (160 mmol, 10 mL) at room temperature. The suspesion was stirred for 2 days at room temperature at which time TLC analysis of the mixture indicated the presence of starting material. An additional 10 mL (160 mmol) of methyl iodide and 2 g (8.6 mmol) of silver oxide were added, respectively. The suspension was stirred for 24 h and the solid was filtered through a pad of celite and was washed with ethyl acetate (30 mL) and methanol (30 mL). The filtrate was concentrated and the residue was extracted with ethyl acetate (3×30 mL).The organic layer was washed with water (20 mL) and brine solution (20 mL) and was dried over anhydrous magnesium sulfate. Filtration of the drying agent and removal of the solvent gave a crude compound which was purified by silica gel column chromatography to obtain 530 mg (50%) as a light brown oil. HR MS (C20H28N2O6): Obs. mass, 392.1940. Calcd. mass, 392.1947 (M+).

1. stirringThe suspension was stirred for 24 h
2. filtrationthe solid was filtered through a pad of celite
3. washwas washed with ethyl acetate (30 mL) and methanol (30 mL)
4. concentrationThe filtrate was concentrated
5. extractionthe residue was extracted with ethyl acetate (3×30 mL).The organic layer
6. washwas washed with water (20 mL) and brine solution (20 mL)
7. dry with materialwas dried over anhydrous magnesium sulfate
8. filtrationFiltration of the drying agent and removal of the solvent

ORD record

ord-effa3cbb11da4ec6aa8aa9f3cc3bc0d3

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06806365B2