Acetic Acid → Cholesterol

HRID 1257938Notes

Reaction equation

HRID 1257938 reaction equation
S[C@:2]1([OH:33])[CH2:30][CH2:29][C@@:28]2([CH3:31])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:27]2[CH2:26][CH2:25][C@@:24]2([CH3:32])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C@H:12]([CH3:23])[CH2:13][CH2:14][CH2:15][CH:16]([CH3:22])[CH2:17]CC(O)C)[CH2:3]1.C(O)(=O)C>CC(N(C)C)=O>[CH3:22][CH:16]([CH2:15][CH2:14][CH2:13][C@H:12]([C@@H:11]1[C@:24]2([CH3:32])[C@H:8]([C@H:7]3[C@H:27]([CH2:26][CH2:25]2)[C@:28]2([CH3:31])[C:4]([CH2:3][C@H:2]([CH2:30][CH2:29]2)[OH:33])=[CH:5][CH2:6]3)[CH2:9][CH2:10]1)[CH3:23])[CH3:17]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 86601308HCID 86601308, compound

Product 1

HCID 5997CholesterolYield 325.8%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent3×

Conditions

Temperature
-2 °C

Procedure

The bromobutylated Tecothane (1.14 g, containing approximately 0.5 mmol of 4-bromobutyl groups) described above was dissolved in DMAc (20 ml) under argon and cooled to −2° C. A solution of 3-mercapto-2-hydroxypropyl-cholesterol (0.495 g, 1.04 mmol) in DMAc (8 ml) was added and a freshly prepared 0.12 M DMAc-solution of (Bu4N)2B4O7 (5 ml, 6 mmol) was also added. The mixture was stirred at −1 to 1° C. for one hour and acidified with acetic acid (0.12 ml, 2 mmol). The reaction solution was then filtered and the polymer was precipitated with methanol (150 ml). The precipitate was washed with methanol alternating with 2-propanol and stirred consequently with large amounts of 2-propanol, methanol, and water and dried under 0.05 mm Hg conditions. The procedure yielded 1.31 g of cholesterol-modified Tecothane. 1H NMR analysis of this polymer (DMF-d7) indicated covalent attachment of cholesterol to 20% of the urethane segments via noncleavable sulfide bonds (see FIG. 2) corresponding to approximately 0.4 mmol of pendant cholesterol moieties per gram of polymer.

Workup

  1. additionThe bromobutylated Tecothane (1.14 g, containing approximately 0.5 mmol of 4-bromobutyl groups)
  2. filtrationThe reaction solution was then filtered
  3. customthe polymer was precipitated with methanol (150 ml)
  4. washThe precipitate was washed with methanol alternating with 2-propanol
  5. stirringstirred consequently with large amounts of 2-propanol, methanol, and water
  6. customdried under 0.05 mm Hg conditions

Sources & evidence

ORD record
ord-91bfd62fa46445d9bbc2cd74f6dbfd71
Source dataset
uspto-grants-2013_06
Patent number
US08465542B2

Reaction notes

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