Ethyl Bromide → HCID 19956414, compound

HRID 1779540Notes

Reaction equation

HRID 1779540 reaction equation
[H-].[Na+].[CH2:3]([N:6]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:7][CH2:8][CH2:9][N:10]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:11]/[CH:12]=[CH:13]/[CH2:14][N:15]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:16][CH2:17][CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:4][CH3:5].[CH2:48](Br)[CH3:49]>CN(C=O)C>[CH2:48]([N:19]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH2:18][CH2:17][CH2:16][N:15]([C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[CH2:14]/[CH:13]=[CH:12]/[CH2:11][N:10]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:9][CH2:8][CH2:7][N:6]([CH2:3][CH2:4][CH3:5])[C:41]([O:43][C:44]([CH3:46])([CH3:45])[CH3:47])=[O:42])[CH3:49]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 19956412HCID 19956412, compound

Product 1

HCID 19956414HCID 19956414, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.05 g (1.25 mmol) of sodium hydride dispersion (approx. 60%) is added, with stirring, to a solution of 0.40 g (0.622 mmol) of (E)-1-propyl-1,5,10,14-tetra-BOC-1,5,10,14-tetraazatetradec-7-ene (see Example 1a) in 6 ml of DMF. The mixture is stirred for 5 min. at room temperature; 0.093 ml (1.25 mmol) of ethyl bromide is added, and the reaction mixture is stirred for a further 36 h at 20° C. and is then concentrated by evaporation in vacuo. Working up analogously to Example 1a) yields the title compound, Rf value=0.55 (silica gel/ethyl acetate:hexane (1:1)).

Workup

  1. stirringthe reaction mixture is stirred for a further 36 h at 20° C.
  2. concentrationis then concentrated by evaporation in vacuo

Sources & evidence

ORD record
ord-9483a2c44bb44d51af45d12cae854da4
Source dataset
uspto-grants-1997_05
Patent number
US05627215

Reaction notes

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