Isopropyl iodide → HCID 19956380, compound

HRID 1779551Notes

Reaction equation

HRID 1779551 reaction equation
[C:1]([NH:8][CH2:9][CH2:10][CH2:11][N:12]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:13]/[CH:14]=[CH:15]/[CH2:16][N:17]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].[CH:45](I)([CH3:47])[CH3:46]>CN(C=O)C>[CH:45]([N:21]([C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])[CH2:20][CH2:19][CH2:18][N:17]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:16]/[CH:15]=[CH:14]/[CH2:13][N:12]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:11][CH2:10][CH2:9][NH:8][C:1]([O:3][C:4]([CH3:5])([CH3:7])[CH3:6])=[O:2])([CH3:47])[CH3:46]

Participants

5

Reactant 3

HCID 6362Isopropyl iodide2×HCID 24758Sodium hydride2×HCID 19956408HCID 19956408, compound

Product 1

HCID 19956380HCID 19956380, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.5 g (2.5 mmol) of (E)-1,5,10,14-tetra-BOC-1,5,10,14-tetraazatetradec7-ene in 20 ml of DMF there are added, with stirring, 0.4 g (10 mmol) of sodium hydride dispersion (approx. 60%) and, after 15 min., 1 ml (10 mmol) of isopropyl iodide. The reaction mixture is stirred for 16 h at room temperature; a further 0.4 g (10 mmol) of sodium hydride dispersion (approx. 60%) and 1 ml (10 mmol) of isopropyl iodide are added, and the mixture is stirred for a further 24 h at 20° C. and for 24 h at 50° C. and is then concentrated by evaporation in vacuo. Working up analogously to Example 1a), using ethyl acetate-hexane (1:3) and ethyl acetate-hexane (1:2) in the flash chromatography, yields the title compound, Rf value=0.37 (silica gel/ethyl acetate:hexane (2:3)).

Workup

  1. stirringThe reaction mixture is stirred for 16 h at room temperature
  2. stirringthe mixture is stirred for a further 24 h at 20° C. and for 24 h at 50° C.
  3. concentrationis then concentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-d44c203cdfdf4745b7605332327310d7
Source dataset
uspto-grants-1997_05
Patent number
US05627215

Reaction notes

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