Dicyclohexylcarbodiimide → 22-Linoleoyloxydocosanoic Acid, Tert.-Butyl Ester

HRID 2399985Notes

Reaction equation

HRID 2399985 reaction equation
[OH:1][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][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].[C:30](O)(=[O:48])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]/[CH:38]=[CH:39]\[CH2:40]/[CH:41]=[CH:42]\[CH2:43][CH2:44][CH2:45][CH2:46][CH3:47].CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>C(O)C>[C:30]([O:1][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][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=[O:48])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]/[CH:38]=[CH:39]\[CH2:40]/[CH:41]=[CH:42]\[CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 5280450Linoleic AcidHCID 19385096Tert.-Butyl 22-Hydroxydocosanoate

Product 1

HCID 8674900122-Linoleoyloxydocosanoic Acid, Tert.-Butyl Ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution containing tert.-butyl 22-hydroxydocosanoate (34) (2.17 g, 5.26 mmol) and linoleic acid (1.45 g, 5.26 mmol) in dry ethanol free chloroform (50 ml) at room temperature under nitrogen was treated with dimethylaminopyridine (0.064 g, 0.524 mmol) and dicyclohexylcarbodiimide (1.19 g, 5.78 mmol), and the resulting solution was stirred for three hours at room temperature, after which time tlc indicated that the reaction is complete. The mixture was filtered and the filtrate washed with 5% acetic acid, then water, then dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica (30 g). Elution with petrol followed by 5% ether in petrol gave the title compound (35) as a white wax (2.18 g, 79%).

Workup

  1. filtrationThe mixture was filtered
  2. washthe filtrate washed with 5% acetic acid
  3. dry with materialwater, then dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica (30 g)
  7. washElution with petrol

Sources & evidence

ORD record
ord-7b438d9c47aa4f86a000f8b3db4aee97
Source dataset
uspto-grants-1995_09
Patent number
US05451691

Reaction notes

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