Diethyl Ether → 1-Octadecylaminocarbonyloxy-3-(4-bromobutylaminocarbonyloxy)-2-methylenepropane

HRID 2166431Notes

Reaction equation

HRID 2166431 reaction equation
[CH2:1]([NH:19][C:20]([O:22][CH2:23][C:24](=[CH2:27])[CH2:25][OH:26])=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[Br:28][CH2:29][CH2:30][CH2:31][CH2:32][N:33]=[C:34]=[O:35].CCOCC>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([NH:19][C:20]([O:22][CH2:23][C:24](=[CH2:27])[CH2:25][O:26][C:34]([NH:33][CH2:32][CH2:31][CH2:30][CH2:29][Br:28])=[O:35])=[O:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 140646443-Octadecylaminocarbonyloxy-2-methylenepropan-1-olHCID 149715841-Bromo-4-isocyanatobutane

Product 1

HCID 230396501-Octadecylaminocarbonyloxy-3-(4-bromobutylaminocarbonyloxy)-2-methylenepropane

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

3-Octadecylaminocarbonyloxy-2-methylenepropan-1-ol (from Preparation 3) (2.0 g) was dissolved in methylene chloride (40 ml). 4-Dimethylaminopyridine (0.13 g) and 4-bromobutyl isocyanate (1.30 g) were added, and the mixture was stirred for 22 hours at 22° C. Ether (40 ml) was added, and the mixture was purified through a column of silica gel 60 (70-230 mesh, 20 g) eluting with ether/chloroform 1:1. Further purification was achieved by chromatography on a Waters PrepLC®/System 500A using a PrepPAK®-500/SILICA cartridge with ether/chloroform/pentane 1:1:2 as eluent.

Workup

  1. customthe mixture was purified through a column of silica gel 60 (70-230 mesh, 20 g)
  2. washeluting with ether/chloroform 1:1
  3. customFurther purification

Sources & evidence

ORD record
ord-8191c91596934131a1840b47c5c55956
Source dataset
uspto-grants-1990_07
Patent number
US04945098

Reaction notes

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