Allyl iodide → HCID 54332185, compound

HRID 1755822Notes

Reaction equation

HRID 1755822 reaction equation
[C:1]([O:5][C:6](=[O:20])[C@H:7]([CH3:19])[NH:8][C:9](OCC1C=CC=CC=1)=O)([CH3:4])([CH3:3])[CH3:2].[CH2:21](I)[CH:22]=C.[H-].[Na+]>C1COCC1>[C:1]([O:5][C:6](=[O:20])[C@H:7]([CH3:19])[NH:8][CH2:9][CH:21]=[CH2:22])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 11129651HCID 11129651, compound

Product 1

HCID 54332185HCID 54332185, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyloxycarbonyl-L-alanine t-butyl ester (10.0 g, 35.8 mmol) was dissolved in dry THF. Allyl iodide (7.4 mL, 78.8 mmol) was added followed by sodium hydride (1.80 g, 45.0 mmol). The reaction was left stirring at room temperature overnight. The reaction was evaporated and taken up in ethyl acetate. It was extracted with water and treated with sodium metabisulfite. The ethyl acetate was extracted with 1N aqueous sodium carbonate, dried over anhydrous magnesium sulfate, filtered and evaporated under vacuum. The crude product was flash chromatographed (silica gel, hexane followed by hexane:ethyl acetate 95:5) to give N-benzyloxycarbonyl, N-allyl-L-alanine t-butyl ester (6.8 g, 60%). 1H NMR (CDCl3) δ7.33 (s, 5H), 6.17-5.67 (m, 1H), 5.20 (d, 4H), 1.75-1.70 (s/d, 12H).

Workup

  1. waitThe reaction was left
  2. customThe reaction was evaporated
  3. extractionIt was extracted with water
  4. additiontreated with sodium metabisulfite
  5. extractionThe ethyl acetate was extracted with 1N aqueous sodium carbonate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customevaporated under vacuum
  9. customchromatographed (silica gel, hexane followed by hexane:ethyl acetate 95:5)

Sources & evidence

ORD record
ord-5963ddbb75f645d0a325f43d703cb40e
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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