Methyl iodide → HCID 19956399, compound

HRID 1779549Notes

Reaction equation

HRID 1779549 reaction equation
[CH2:1]([N:4]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:5][CH2:6][CH2:7][N:8]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:9]/[CH:10]=[CH:11]/[CH2:12][N:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:2]=[CH2:3].[H-].[Na+].[CH3:48]I>CN(C=O)C>[CH2:1]([N:4]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:5][CH2:6][CH2:7][N:8]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:9]/[CH:10]=[CH:11]/[CH2:12][N:13]([C:25]([O:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[O:26])[CH2:14][CH2:15][CH2:16][N:17]([CH3:48])[C:18]([O:20][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:19])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 19956406HCID 19956406, compound

Product 1

HCID 19956399HCID 19956399, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.6 g (0.936 mmol) of (E)-1-allyl-1,5,10,14-tetra-BOC-1,5,10,14-tetraazatetradec-7-ene (see Example 2a) in 8 ml of DMF there are added, with stirring, 0.075 g (1.875 mmol) of sodium hydride dispersion (approx. 60%) and, after 5 min., 0.117 ml (1.875 mmol) of methyl iodide. The reaction mixture is stirred for 15 h at room temperature; a further 0.075 g (1.875 mmol) of sodium hydride dispersion (approx. 60% ) and 0.117 ml (1.875 mmol) of methyl iodide are added, and the mixture is stirred for a further 96 h at 20° C. and is then concentrated by evaporation in vacuo. Working up analogously to Example 1a, but using ethyl acetate-hexane (1:2) in the flash chromatography, yields the title compound, Rf value=0.36 (silica gel/ethyl acetate:hexane (2:3)).

Workup

  1. stirringThe reaction mixture is stirred for 15 h at room temperature
  2. stirringthe mixture is stirred for a further 96 h at 20° C.
  3. concentrationis then concentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-e23c76b673024c27aae8ac7c9a071c6d
Source dataset
uspto-grants-1997_05
Patent number
US05627215

Reaction notes

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