Iodoethane → N-[(1,1-Dimethylethoxy)carbonyl]-N-ethyl-L-alanine

HRID 1486097Notes

Reaction equation

HRID 1486097 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:13])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:14](I)[CH3:15].[H-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH2:14][CH3:15])[C@@H:9]([CH3:13])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 71423142N-[(1,1-Dimethylethoxy)carbonyl]-N-ethyl-L-alanineYield 87.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (S)-2-(tert-butoxycarbonylamino)propanoic acid (0.7 g, 3.7 mmol) and ethyl iodide (2.6 ml, 32.2 mmol) in THF (10 ml) was added sodium hydride (60% w/w dispersion in mineral oil, 576 mg, 14.4 mmol). The reaction was sealed and stirred at 60° C. overnight, then partitioned between EtOAc and H2O. The aqueous layer was acidified to pH 4 with citric acid solution and extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to provide (S)-2-(tert-butoxycarbonyl(ethyl)amino)propanoic acid (700 mg, 87%) as an oil.

Workup

  1. customThe reaction was sealed
  2. custompartitioned between EtOAc and H2O
  3. extractionextracted with EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3c9421c99ef048abab6d79f89116cb5b
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

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