Sodium Chloride → triBoc Spermine Ethyl Acetate

HRID 1625688Notes

Reaction equation

HRID 1625688 reaction equation
C(N(CC)CC)C.[C:8]([CH:15]([CH2:31][CH2:32][NH:33][CH2:34][CH2:35][CH2:36][CH2:37][NH:38][CH2:39][CH2:40][CH2:41][NH2:42])[N:16]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].BrCC(OCC)=O.[Na+].[Cl-]>C(#N)C>[CH2:11]([O:10][C:8](=[O:9])[CH3:15])[CH3:12].[C:8]([CH:15]([CH2:31][CH2:32][NH:33][CH2:34][CH2:35][CH2:36][CH2:37][NH:38][CH2:39][CH2:40][CH2:41][NH2:42])[N:16]([C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])[C:24]([O:26][C:27]([CH3:29])([CH3:30])[CH3:28])=[O:25])([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 22610912TriBoc-Spermine

Product 1

HCID 131731668triBoc Spermine Ethyl AcetateYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.6 ml of triethylamine (18.4 mmol, 2.5 eq) is added to a solution of 3.96 g of triBoc spermine (7.3 mmol, 1 eq) in 100 ml of acetonitrile. 0.81 ml of ethyl bromoacetate (7.3 mmol, 1 eq) is then quickly added to this solution under stirring. After 5 h of stirring at room temperature, the reaction medium is dumped into a saturated NaCl solution (100 ml) and extracted with ethyl acetate (2*100 ml). After the organic phases are dried, filtered and evaporated, the residue obtained is purified by flash chromatography on SiO2 (elution with a gradient from pure heptane to pure CH2Cl2, then with 90/10 CH2Cl2/MeOH). 2.77 g of a colorless oil is obtained (Yield=64%; TLC Rf=0.57; 90/10 CH2Cl2/MeOH) and 1.05 g of the starting triBoc spermine is recovered (adjusted yield=87%).

Workup

  1. stirringAfter 5 h of stirring at room temperature
  2. extractionextracted with ethyl acetate (2*100 ml)
  3. customAfter the organic phases are dried
  4. filtrationfiltered
  5. customevaporated
  6. customthe residue obtained
  7. customis purified by flash chromatography on SiO2 (
  8. washelution with a gradient from pure heptane to pure CH2Cl2

Sources & evidence

ORD record
ord-0e67ed27930f4d1fbfd6b4a242c54872
Source dataset
uspto-grants-2014_07
Patent number
US08785424B2

Reaction notes

Loading…