Methyl iodide → Boc-L-phenylalanine methyl ester

HRID 1886523Notes

Reaction equation

HRID 1886523 reaction equation
[CH3:1][C:2]([CH3:19])([O:4][C:5]([NH:7][C@H:8]([C:16]([OH:18])=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6])[CH3:3].[C:20](=O)(O)[O-].[Na+].IC>CN(C)C=O>[CH3:3][C:2]([CH3:19])([O:4][C:5]([NH:7][C@H:8]([C:16]([O:18][CH3:20])=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6])[CH3:1]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 516892Sodium Bicarbonate

Product 1

HCID 9882138Boc-L-phenylalanine methyl esterYield 99.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution containing N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine (10 g, 37.7 mmole) in dimethylformamide (40 ml) is added solid sodium bicarbonate (4.75 g, 56.6 mmole) and iodomethane (16 g, 113 mmole). The mixture is heated at 40° under argon for 12 hours, the cooled and the reaction mixture partitioned between water (150 ml) and ether (250 ml). The organic layer is rinsed with 2% aqueous sodium bicarbonate (2×100 ml), 2% aqueous sodium bisulfite (100 ml), water (2 ×100 ml), and brine, dried over magnesium sulfate, and concentrated in vacuo to give 10.5 g of N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine, methyl ester as an oil.

Workup

  1. temperatureThe mixture is heated at 40° under argon for 12 hours
  2. temperaturethe cooled
  3. customthe reaction mixture partitioned between water (150 ml) and ether (250 ml)
  4. washThe organic layer is rinsed with 2% aqueous sodium bicarbonate (2×100 ml), 2% aqueous sodium bisulfite (100 ml), water (2 ×100 ml), and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0995dffee99d46a8b18f9e560c4be237
Source dataset
uspto-grants-1992_09
Patent number
US05151513

Reaction notes

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