Methyl iodide → HCID 19956386, compound

HRID 1779536Notes

Reaction equation

HRID 1779536 reaction equation
[CH2:1]([N:3]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[CH2:4][CH2:5][CH2:6][N:7]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:8]/[CH:9]=[CH:10]/[CH2:11][N:12]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH3:2].[H-].[Na+].[CH3:47]I>CN(C=O)C>[CH2:1]([N:3]([C:38]([O:40][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:39])[CH2:4][CH2:5][CH2:6][N:7]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:8]/[CH:9]=[CH:10]/[CH2:11][N:12]([C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:13][CH2:14][CH2:15][N:16]([CH3:47])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 24758Sodium hydride2×HCID 19956393HCID 19956393, compound

Product 1

HCID 19956386HCID 19956386, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.46 g (0.73 mmol) of (E)-1-ethyl-1,5,10,14-tetra-BOC-1,5,10,14-tetraazatetradec-7-ene (see Example 5a) in 6 ml of DMF there are added, with stirring, 0.059 g (1.47 mmol) of sodium hydride dispersion (approx. 60% ) and, after 5 min., 0.092 ml (1.47 mmol) of methyl iodide. The reaction mixture is stirred for 15 h at room temperature; a further 0.029 g (0.725 mmol) of sodium hydride dispersion (approx. 60%) and 0.045 ml (0.721 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=0.42 (silica gel/ethyl acetate:hexane (1:1)).

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-fd03586a913d481b902b960bae872466
Source dataset
uspto-grants-1997_05
Patent number
US05627215

Reaction notes

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