Benzene, 2-fluoro-4-methyl-1-nitro- → (S)-3-(5-Methyl-2-nitro-phenylamino)-5-phenyl-pentanoic acid ethyl ester

To a solution of 3-Fluoro-4-nitrotoluene (0.7 g, 4.5 mmol) in DMF (5 mL) were added (S)-3-Amino-5-phenyl-pentanoic acid ethyl ester hydrochloride (1.2 g, 4.5 mmol) and DIPEA (1.6 g, 9.0 mmol). The reaction mixture was stirred at room temperature for 48 h. The reaction mixture was then diluted with ethyl acetate and washed with water (×4). The organic phase was then dried over Na2SO4 and concentrated to afford an orange solid. The resulting residue was Purified by silica gel prep TLC using 4:1 Hexanes:ethyl acetate as an eluent to afford 0.9 g of the desired product.

1. washwashed with water (×4)
2. dry with materialThe organic phase was then dried over Na2SO4
3. concentrationconcentrated
4. customto afford an orange solid
5. customThe resulting residue was Purified by silica gel prep TLC

ORD record

ord-272b25c17459421388c7594fe89901f5

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150556B2