Cholesterol → HCID 86648143, compound

HRID 469178Notes

Reaction equation

HRID 469178 reaction equation
[CH3:1][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16]([CH2:17][C@H:18]([CH2:20][CH2:21]2)[OH:19])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:3].[Br:29][CH2:30][C:31](O)=[O:32]>ClCCl.CN(C)C1C=CN=CC=1.CCCCCC.CCOC(C)=O>[Br:29][CH2:30][C:31]([CH2:3][CH:2]([CH2:4][CH2:5][CH2:6][C@H:7]([C@@H:9]1[C@:27]2([CH3:28])[C@H:12]([C@H:13]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:16]([CH2:17][C@H:18]([CH2:20][CH2:21]2)[OH:19])=[CH:15][CH2:14]3)[CH2:11][CH2:10]1)[CH3:8])[CH3:1])=[O:32]

Participants

6

Reactant 2

HCID 5997CholesterolHCID 6227Bromoacetic Acid

Product 1

HCID 86648143HCID 86648143, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 100 mg of cholesterol and 40 mg of bromoacetic acid (1.1 eq) was dissolved in 10 mL of anhydrous dichloromethane. Then 44 μl (1.1 eq) of DIPC(N,N-diisopropylcarbodiimide) and 1.5 mg (0.05 eq) of DMAP (4-dimethylaminopyridine) were added. The solution was left stirring at room temperature for 48 h and analyzed by TLC using a mixture of n-hexane/EtOAc 10/1 as solvent systems. The solvent was evaporated and the reaction product was purified by silica gel flash chromatography in n-hexane/dichloromethane 1/1. The fractions containing the product were pooled, evaporated and then lyophilized in water/acetonitrile 20/80. The purified product was analyzed by NMR. Yield: 73%.

Workup

  1. waitThe solution was left
  2. customThe solvent was evaporated
  3. customthe reaction product was purified by silica gel flash chromatography in n-hexane/dichloromethane 1/1
  4. additionThe fractions containing the product
  5. customevaporated

Sources & evidence

ORD record
ord-f92f883b18c2454f9fa8077ecabde0e7
Source dataset
uspto-grants-2014_01
Patent number
US08629101B2

Reaction notes

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