Reaction #2320142

Reaction equation

ethyl acetate

methyl iodide

N-Boc-4-iodophenylalanine

NaHCO3

→

yellow oily solid

Yield 111.8%

N-Boc-4-iodophenylalanine methylester

Yield 111.8%

Solvents

DMF

Conditions

Workup

1. 1
   Washthe mixture was washed with 3×100 mL of deionized water
2. 2
   OtherThe organic layer was separated
3. 3
   Dryingdried over Na2SO4
4. 4
   Concentrationconcentrated under vacuum

Procedure

To a solution of 5.02 g (12.8 mmol) of N-Boc-4-iodophenylalanine in 60 mL of DMF was added NaHCO3 (1.42 g, 16.9 mmol) followed by methyl iodide (3.0 mL, 48.2 mmol). The mixture was stirred under argon for 40 h at room temperature. After this time, 150 mL of ethyl acetate was added, and the mixture was washed with 3×100 mL of deionized water. The organic layer was separated, dried over Na2SO4, and concentrated under vacuum to yield 5.80 g of a yellow oily solid. The crude product was purified by flash chromatography (1:5 ethyl acetate:hexanes) to afford a white solid (4.72 g, 91%). mp 79-80° C.; 1H NMR (400 MHz, CDCl3) δ 1.43 (s, 9 H), 3.04 (2 dd, J=4.8 Hz, 12.8 Hz), 3.72 (s, 3 H), 4.58 (m, 1 H), 4.97 (brs, NH, 1 H), 6.88 (d, J=7.8 Hz, 2 H), 7.62 (d, J=7.8 Hz, 2 H); HRMS (ESI, M+1) calcd for C15H21INO4406.0510, found 406.0515.

Source