Methyl iodide → methyl N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-2-methylalaninate

HRID 1042425Notes

Reaction equation

HRID 1042425 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:15][CH2:16][C:17]#[N:18])[C:9]([CH3:14])([C:11]([OH:13])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:19]I>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([CH2:15][CH2:16][C:17]#[N:18])[C:9]([CH3:10])([C:11]([O:13][CH3:19])=[O:12])[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6328Methyl iodide2×HCID 575236442-((tert-Butoxycarbonyl)(2-cyanoethyl)amino)-2-methylpropanoic acid

Product 1

HCID 57523645methyl N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-2-methylalaninateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

62 g (0.23 mol) of N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-2-methylalanine were dissolved in 350 ml of DMF and 50 g of KHCO3 were added. Few minutes after, 30 ml of methyl iodide (MeI) were dropped and the mixture was stirred at room temperature for 6 hours. Then a further 15 ml of MeI were added. The mixture was left at room temperature overnight. After dilution with 1.5 l of water, the solution was extracted with ethyl acetate (3 times). The organic phases were washed with a small amount of water, dried over sodium sulfate, evaporated and dried at the mechanical pump. 60.5 g (97%) of methyl N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-2-methylalaninate were thus obtained.

Workup

  1. waitThe mixture was left at room temperature overnight
  2. extractionAfter dilution with 1.5 l of water, the solution was extracted with ethyl acetate (3 times)
  3. washThe organic phases were washed with a small amount of water
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customdried at the mechanical pump

Sources & evidence

ORD record
ord-dd59f248017346a78a5105b9afae474a
Source dataset
uspto-grants-2013_10
Patent number
US08557857B2

Reaction notes

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