3,3,5-Trimethylcyclohexanol → HCID 86747828, compound

HRID 1033230Notes

Reaction equation

HRID 1033230 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:23]=[CH:22][C:14]([O:15][C:16]([CH3:21])([CH3:20])[C:17]([OH:19])=[O:18])=[CH:13][CH:12]=2)=[O:7])=[CH:4][CH:3]=1.[CH3:26][C:27]1([CH3:35])[CH2:32][CH:31]([CH3:33])[CH2:30][CH:29](O)[CH2:28]1.CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([O:15][C:16]([CH3:20])([CH3:21])[C:17]([O:19][C@H:29]3[CH2:30][C@H:31]([CH3:33])[CH2:32][C:27]([CH3:35])([CH3:26])[CH2:28]3)=[O:18])=[CH:22][CH:23]=2)=[O:7])=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 82983,3,5-TrimethylcyclohexanolHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 39042Bezafibrate

Product 1

HCID 86747828HCID 86747828, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

12.5 g (0.034 mol) of 2-(4-(2-parachlorobenzamidoethyl)phenoxy)-2-methylpropionic acid are dissolved in 100 ml of anhydrous dimethylformamide, and 4.8 g of 3,3,5-trimethylcyclohexanol (transform) (0.034 mol) and 0.5 g of dimethylaminopyridine are added. After solubilization, a solution of 7 g of dicyclohexylcarbodiimide (0.034 mol) in 20 ml of dimethylformamide is added slowly at a temperature of around 0° C. The reaction is allowed to continue for 24 hours at ordinary temperature and the precipitate of dicyclohexylurea is filtered off; after evaporation of the filtrate under reduced pressure, the residue is chromatographed on a silica column in a mixture of petroleum ether and ethyl acetate. After evaporation of the solvent, the title derivative is obtained in the form of white crystals melting at 100° C.; the yield is 45%. This product, chromatographed under the conditions of Example 1, shows a single spot of Rf 0.2. The IR spectrum run in KBr has the following characteristic bands: one broad band at 3250 cm-1, a group of fine bands at 3000-2840 cm-1 an strong bands at 1750 cm-1 and 1640 cm-1.

Workup

  1. filtrationthe precipitate of dicyclohexylurea is filtered off
  2. customafter evaporation of the filtrate under reduced pressure
  3. customthe residue is chromatographed on a silica column in a mixture of petroleum ether and ethyl acetate
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-ae14080d5f44417ab20d4b46b2520081
Source dataset
uspto-grants-1994_05
Patent number
US05310757

Reaction notes

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