Triethylamine → (Z)-((2-bromoacetyl)azanediyl)bis(ethane-2,1-diyl) dioleate

HRID 1471452Notes

Reaction equation

HRID 1471452 reaction equation
OC(C(F)(F)F)=O.[C:8]([O:27][CH2:28][CH2:29][NH:30][CH2:31][CH2:32][O:33][C:34](=[O:52])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]/[CH:42]=[CH:43]\[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])(=[O:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].[Br:53][CH2:54][C:55](Br)=[O:56].C(N(CC)CC)C>C(Cl)Cl>[C:8]([O:27][CH2:28][CH2:29][N:30]([C:55](=[O:56])[CH2:54][Br:53])[CH2:31][CH2:32][O:33][C:34](=[O:52])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]/[CH:42]=[CH:43]\[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH3:51])(=[O:26])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 131732750(Z)-azanediylbis(ethane-2,1-diyl) dioleate TFA salt2×

Product 1

HCID 89394381(Z)-((2-bromoacetyl)azanediyl)bis(ethane-2,1-diyl) dioleate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Synthesis of (Z)-azanediylbis(ethane-2,1-diyl) dioleate TFA salt previously described. (Z)-azanediylbis(ethane-2,1-diyl) dioleate TFA salt (1.50 g, 2.34 mmol) was dissolved in DCM (20 mL) and placed in an ice-bath. Bromoacetyl bromide (214 uL, 2.46 mmol) was added followed by triethylamine (685 uL, 4.91 mmol). The ice-bath was removed and the reaction was allowed to stir overnight at room temperature under inert gas, then diluted with DCM to 100 mL, and washed with a 1M HCl (75 mL), H2O (75 mL), saturated NaHCO3 solution (75 mL) and saturated brine solution (75 mL). All aqueous washes were back extracted with DCM (25 mL). Dried organics with MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography with ethyl acetate yielded (Z)-((2-bromoacetyl)azanediyl)bis(ethane-2,1-diyl) dioleate (1.22 g).

Workup

  1. customplaced in an ice-bath
  2. customThe ice-bath was removed
  3. additiondiluted with DCM to 100 mL
  4. washwashed with a 1M HCl (75 mL), H2O (75 mL), saturated NaHCO3 solution (75 mL) and saturated brine solution (75 mL)
  5. extractionAll aqueous washes were back extracted with DCM (25 mL)
  6. filtrationDried organics with MgSO4, filtered
  7. concentrationconcentrated in vacuo
  8. customPurification by silica gel chromatography with ethyl acetate

Sources & evidence

ORD record
ord-6f30bae6a15e4aa8af7687e13d103784
Source dataset
uspto-grants-2015_04
Patent number
US09011903B2

Reaction notes

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