Butyl bromide → HCID 19956404, compound

HRID 1779538Notes

Reaction equation

HRID 1779538 reaction equation
[H-].[Na+].[CH2:3]([N:5]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:6][CH2:7][CH2:8][N:9]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:10]/[CH:11]=[CH:12]/[CH2:13][N:14]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH3:4].[CH2:47](Br)[CH2:48][CH2:49][CH3:50]>CN(C=O)C>[CH2:47]([N:18]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[CH2:17][CH2:16][CH2:15][N:14]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:13]/[CH:12]=[CH:11]/[CH2:10][N:9]([C:33]([O:35][C:36]([CH3:37])([CH3:38])[CH3:39])=[O:34])[CH2:8][CH2:7][CH2:6][N:5]([CH2:3][CH3:4])[C:40]([O:42][C:43]([CH3:44])([CH3:45])[CH3:46])=[O:41])[CH2:48][CH2:49][CH3:50]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 24758Sodium hydrideHCID 19956393HCID 19956393, compound

Product 1

HCID 19956404HCID 19956404, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.059 g (1.47 mmol) of sodium hydride dispersion (approx. 60%) is added, with stirring, to a solution of 0.46 g (0.73 retool) 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. The mixture is stirred for 5 min. at room temperature; 0.159 ml (1.47 mmol) of butyl bromide is added, and the reaction mixture is stirred for a further 15 h at 20° C. and is then concentrated by evaporation in vacuo. Working up analogously to Example 1a) yields the title compound, Rf value=0.56 (silica gel/ethyl acetate:hexane (1:1)).

Workup

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

Sources & evidence

ORD record
ord-c64ccdc5b5ba47a2be6edbe3f6442a0b
Source dataset
uspto-grants-1997_05
Patent number
US05627215

Reaction notes

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