Water → HCID 11064697, compound

HRID 1744785Notes

Reaction equation

HRID 1744785 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@H:9]([C:24]([OH:26])=[O:25])[CH2:10][CH2:11][CH2:12][NH:13]C(OCC1C=CC=CC=1)=O)=[O:7])([CH3:4])[CH3:3].[H-].[Na+].[CH3:29]I.O>C1COCC1>[N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])([CH3:29])[C@H:9]([C:24]([OH:26])=[O:25])[CH2:10][CH2:11][CH2:12][NH2:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 7269338(2S)-5-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}pentanoic acid

Product 1

HCID 11064697HCID 11064697, compoundYield 159.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.00 g (8.19 mmol) of Boc-Orn (Z)-OH in 82 ml of THF were added 1.31 g (32.8 mmol) of 60% sodium hydride and 4.08 ml (65.5 mmol) of methyl iodide with ice cooling, and the mixture was stirred at room temperature for 16 hours. The reaction solution was combined with water with ice cooling, and washed with hexane. The aqueous layer was combined with 10% aqueous citric acid solution, extracted with ethyl acetate and the extract was washed with saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate, and then the solvent was distilled off under reduced pressure to give 3.22 g (100%) of Boc-N-Me-Orn (Me) (Z)-OH.

Workup

  1. washwashed with hexane
  2. extractionextracted with ethyl acetate
  3. washthe extract was washed with saturated aqueous sodium chloride solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1065cd29bb3246d28830838f993bd1a5
Source dataset
uspto-grants-2006_03
Patent number
US07018981B2

Reaction notes

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