Cholesterol → HCID 69177522, compound

HRID 860703Notes

Reaction equation

HRID 860703 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].[C:29](O)(=[O:35])[CH2:30][CH2:31][CH2:32][CH:33]=[CH2:34].C1CCC(N=C=NC2CCCCC2)CC1.C(OC)(C)(C)C>C(Cl)Cl>[C:29]([C@:18]1([OH:19])[CH2:20][CH2:21][C@@:22]2([CH3:23])[C:16](=[CH:15][CH2:14][C@@H:13]3[C@@H:24]2[CH2:25][CH2:26][C@@:27]2([CH3:28])[C@H:12]3[CH2:11][CH2:10][C@@H:9]2[C@H:7]([CH3:8])[CH2:6][CH2:5][CH2:4][CH:2]([CH3:1])[CH3:3])[CH2:17]1)(=[O:35])[CH:30]=[CH:31][CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 4

HCID 5997CholesterolHCID 10868DicyclohexylcarbodiimideHCID 153085-Hexenoic AcidHCID 15413tert-Butyl methyl ether

Product 1

HCID 69177522HCID 69177522, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cholesterol (2.0 g, 5.17 mM) in methylene chloride (20 mL) was added 5-hexenoic acid (0.68 mL, 5.69 mM) followed by the addition of DCC (1.60 g, 7.76 mM) and 4-PP (0.115 g, 0.78 mM) under nitrogen atmosphere. The resulting reaction mixture was stirred at ambient temperature for 1 h and worked up with the addition of methyl t-butyl ether (60 mL). The urea was filtered off, and the product was transferred to a separatory funnel, washed with 1N HCl (10 mL), water (30 mL) and brine (30 mL). The product was filtered after drying over MgSO4 and the solvent was evaporated to leave a residue. The product obtained in >95% yield was characterized by 1H NMR.

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe urea was filtered off
  3. customthe product was transferred to a separatory funnel
  4. washwashed with 1N HCl (10 mL), water (30 mL) and brine (30 mL)
  5. filtrationThe product was filtered
  6. dry with materialafter drying over MgSO4
  7. customthe solvent was evaporated
  8. customto leave a residue
  9. customThe product obtained in >95% yield

Sources & evidence

ORD record
ord-e6c85256c5b54ec58b2b7c98de08a5f5
Source dataset
uspto-grants-2006_12
Patent number
US07153946B2

Reaction notes

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