Dicyclohexylcarbodiimide → HCID 67793564, compound

HRID 892894Notes

Reaction equation

HRID 892894 reaction equation
[C:1]([NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[OH:27])(=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:28][C:29]1([CH3:45])[O:34][CH:33]([C:35]([NH:37][CH2:38][CH2:39][C:40](O)=[O:41])=[O:36])[C:32]([CH3:44])([CH3:43])[CH2:31][O:30]1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1>[CH3:28][C:29]1([CH3:45])[O:34][CH:33]([C:35]([NH:37][CH2:38][CH2:39][C:40]([O:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[NH:20][C:1](=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[O:41])=[O:36])[C:32]([CH3:44])([CH3:43])[CH2:31][O:30]1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 189385173-[N-(2,2,5,5-Tetramethyl-1,3-dioxane-4-carbonyl)amino]propionic acidHCID 52916764HCID 52916764, compound

Product 1

HCID 67793564HCID 67793564, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

A solution of 303 mg of 2-oleoylaminophenol, mg of 3-[N-(2,2,5,5-tetramethyl-1,3-dioxane-4-carbonyl)amino]propionic acid, 227 mg of dicyclohexylcarbodiimide and 122 mg of 4-dimethylamino pyridine in 15 ml of toluene was heated under reflux for 2 hours. After cooling the reaction mixture, the crystals formed were filtered. The filtrate was concentrated and the residue obtained was subjected to silica gel column chromatography to obtain 445 mg of the title compound (yield: 72%).

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureAfter cooling the reaction mixture
  3. customthe crystals formed
  4. filtrationwere filtered
  5. concentrationThe filtrate was concentrated
  6. customthe residue obtained

Sources & evidence

ORD record
ord-73cae033527040d4b536dcbe0f25cf5c
Source dataset
uspto-grants-1992_06
Patent number
US05120738

Reaction notes

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