Methyl iodide → N-Boc-4-iodophenylalanine methylester

HRID 452369Notes

Reaction equation

HRID 452369 reaction equation
[C:1]([NH:8][C@H:9]([C:18]([OH:20])=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([I:17])=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:21]([O-])(O)=O.[Na+].CI.C(OCC)(=O)C>CN(C=O)C>[CH3:21][O:19][C:18](=[O:20])[C@H:9]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([I:17])=[CH:15][CH:16]=1)[NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 2755956(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(4-iodophenyl)propanoic acid

Product 1

HCID 10319078N-Boc-4-iodophenylalanine methylesterYield 111.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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, 9H), 3.04 (2dd, J=4.8 Hz, 12.8 Hz), 3.72 (s, 3H), 4.58 (m, 1H), 4.97 (brs, NH, 1H), 6.88 (d, J=7.8 Hz, 2H), 7.62 (d, J=7.8 Hz, 2H); HRMS (ESI, M+1) calcd for C15H21INO4 406.0510. Found 406.0515.

Workup

  1. washthe mixture was washed with 3×100 mL of deionized water
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0daa6d795a1c4d7ca8910c6a6c2da4cc
Source dataset
uspto-grants-2013_07
Patent number
US08492345B2

Reaction notes

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