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

HRID 1479039Notes

Reaction equation

HRID 1479039 reaction equation
[CH3:1]I.[C:3]([O:7][C:8]([N:10]([CH2:17][CH2:18][C:19]#[N:20])[C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4]>CN(C=O)C>[C:3]([O:7][C:8]([N:10]([CH2:17][CH2:18][C:19]#[N:20])[C:11]([CH3:15])([CH3:16])[C:12]([O:14][CH3:1])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

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

Product 1

HCID 57523645methyl N-(tert-butoxycarbonyl)-N-(2-cyanoethyl)-2-methylalaninateYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl iodide (12.5 mL, 193.2 mmol) was added to a mixture of 2-[(tert-butoxycarbonyl)(2-cyanoethyl)amino]-2-methylpropanoic acid (16.5 g, 64.4 mmol) and KHCO3 (12.9 g, 193.2 mmol) in DMF (150 mL) and the reaction mixture was stirred at room temperature for 16 hours. After dilution with water, the solution was extracted with a 1/1 mixture of hexane/EA (2×). The combined organics were dried over magnesium sulfate and concentrated in vacuo to afford the title compound (16.5 g, 95%) as a yellow oil. 1H NMR (DMSO-d6) δ 3.61-3.55 (m, 5H), 2.71 (t, J=6.76 Hz, 2H), 1.42-1.36 (m, 15H).

Workup

  1. extractionAfter dilution with water, the solution was extracted with a 1/1 mixture of hexane/EA (2×)
  2. dry with materialThe combined organics were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-901456e0fd4c4dee8b6db89cdb067ac6
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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