Water → HCID 131727523, compound

HRID 1988295Notes

Reaction equation

HRID 1988295 reaction equation
[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.[CH2:21](I)[CH3:22].[H-].[Na+].O>C1COCC1.CN(C=O)C>[N:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([CH2:21][CH3:22])[C@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([F:10])=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 7020910N-(tert-Butoxycarbonyl)-4-fluoro-L-phenylalanine

Product 1

HCID 131727523HCID 131727523, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of Boc-Phe(4-F)-OH (1.0 g, 3.53 mmol) in THF/DMF (6 ml/1.5 ml), ethyl iodide (2.24 ml, 20.8 mmol) and 60% sodium hydride (422 mg, 10.6 mmol) were added under cooling with ice and stirred at room temperature for 19 hours. The reaction mixture was mixed with water slowly and then with a saturated aqueous NH4Cl solution and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The thus obtained residue was subjected to silica gel column chromatography (n-hexane:ethyl acetate:methylene chloride=1:1:15), giving Boc-N-Et-Phe(4-F)-OH (P10) (593 mg, 54%).

Workup

  1. temperatureunder cooling with ice
  2. extractionwith a saturated aqueous NH4Cl solution and extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-26efc1212f7a4fd5b742671adee3962c
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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