Methyl iodide → HCID 68564892, compound

HRID 2061031Notes

Reaction equation

HRID 2061031 reaction equation
[CH3:1][N:2]([CH3:24])[CH2:3][CH2:4][N:5]([CH3:23])[C:6](=[O:22])[CH2:7][C:8]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:10])[CH3:9].[CH3:25][I:26]>C(O)C>[I-:26].[CH2:14]([O:13][C:12]([NH:11][C:8]([CH3:10])([CH3:9])[CH2:7][C:6]([N:5]([CH2:4][CH2:3][N+:2]([CH3:25])([CH3:1])[CH3:24])[CH3:23])=[O:22])=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 60134427HCID 60134427, compound

Product 1

HCID 68564892HCID 68564892, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Benzyl 4-((2-(dimethylamino)ethyl)(methyl)amino)-2-methyl-4-oxobutan-2-ylcarbamate (2.08 g, 6.2 mmol) was dissolved in a solution of ethanol (4 ml) and methyl iodide (30 ml). The mixture was stirred at 50° C. for 18 hours. The reaction mixture was concentrated in vacuo and dissolved in water. The aqueous mixture was washed with ethyl acetate. The washed aqueous mixture concentrated in vacuo to give 2.19 g (74%) of 2-(3-(benzyloxycarbonylamino)-N,3-dimethylbutanamido)-N,N,N-trimethylethanaminium iodide. MS (ESI+) calculated for C19H32N3O3+: 350.24, Found: 350.2 (M+).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutiondissolved in water
  3. washThe aqueous mixture was washed with ethyl acetate
  4. concentrationThe washed aqueous mixture concentrated in vacuo

Sources & evidence

ORD record
ord-f8b45931b3e04a869b48a5c05c633be2
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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