Dicyclohexylcarbodiimide → 3-(6-Decanamidohexanoyloxy)octadecanoic acid t-butyl ester

HRID 1249216Notes

Reaction equation

HRID 1249216 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][CH:8]([OH:24])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([CH3:4])([CH3:3])[CH3:2].[C:26]([NH:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][C:43](O)=[O:44])(=[O:36])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]([O:5][C:6](=[O:25])[CH2:7][CH:8]([O:24][C:43](=[O:44])[CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][NH:37][C:26](=[O:36])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 5993336-(Decanoylamino)hexanoic acidHCID 13962663Tert-butyl 3-hydroxyoctadecanoate

Product 1

HCID 537763563-(6-Decanamidohexanoyloxy)octadecanoic acid t-butyl esterYield 22.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1.57 g of 3-hydroxyoctadecanoic acid t-butyl ester and 1.30 g of 6-decanamidohexanoic acid were mixed with 30 ml of methylenechloride and after adding thereto 50 mg of DMAP and 930 mg of DCC while stirring, the mixture was stirred for 2 days at room temperature. Precipitates formed were removed by filtration and the filtrate was washed with 10 ml of 0.1N hydrochloric acid, and then washed twice with water, dried over anhydrous magnesium sulfate, and concentrated. The concentrate was subjected to column chromatography and eluted with chloroform to provide 610 mg of 3-(6-decanamidohexanoyloxy)octadecanoic acid t-butyl ester.

Workup

  1. additionafter adding
  2. customPrecipitates
  3. customformed
  4. customwere removed by filtration
  5. washthe filtrate was washed with 10 ml of 0.1N hydrochloric acid
  6. washwashed twice with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. washeluted with chloroform

Sources & evidence

ORD record
ord-af38dda83b354fa6a950940eda76bcf5
Source dataset
uspto-grants-1986_12
Patent number
US04629736

Reaction notes

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