Azobisisobutyronitrile → HCID 86757133, compound

HRID 1384057Notes

Reaction equation

HRID 1384057 reaction equation
[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8]([O:10][C@@H:11]1[CH2:38][CH2:37][C@@:36]2([CH3:39])[C@H:13]([CH2:14][C@@H:15]([OH:42])[C@@H:16]3[C@@H:35]2[CH2:34][C@H:33]([OH:40])[C@@:32]2([CH3:41])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C@H:21]([CH3:31])[CH2:22][CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:12]1)=[O:9].[C:43]1(=[O:49])[O:48][C:46](=[O:47])[CH:45]=[CH:44]1.N(C(C)(C)C#N)=NC(C)(C)C#N>C1(C)C=CC=CC=1>[CH:1]12[CH2:7][CH:4]([CH:5]=[CH:6]1)[CH2:3][CH:2]2[C:8]([O:10][C@@H:11]1[CH2:38][CH2:37][C@@:36]2([CH3:39])[C@H:13]([CH2:14][C@@H:15]([OH:42])[C@@H:16]3[C@@H:35]2[CH2:34][C@H:33]([OH:40])[C@@:32]2([CH3:41])[C@H:17]3[CH2:18][CH2:19][C@@H:20]2[C@H:21]([CH3:31])[CH2:22][CH2:23][C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[CH2:12]1)=[O:9].[C:46]1(=[O:47])[O:48][C:43](=[O:49])[CH:44]=[CH:45]1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 7923Maleic AnhydrideHCID 86757134HCID 86757134, compound

Product 1

HCID 86757133HCID 86757133, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1 g (0.0017 mole) of t-butyl 3α-(5-norbornene-2-carbonyloxy)-7α, 12α-dihydroxy-5β-cholan-24-oate prepared in Example 4, 0.17 g (0.0017 mole) of purified maleic anhydride, and 0.0056 g (2 mole %) of 2,2′-azobisisobutyronitrile as a radical polymerization initiator, were dissolved in 3 ml of toluene solvent. The solution was introduced into a polymerization glass tube ampule which was then sealed under vacuum. Then, the solution was polymerized at a temperature of 65° C. for 20 hours. After the polymerization, the polymerization product was precipitated in petroleum ether/ethyl ether(5/1, volume ratio), and the precipitate was recovered with a glass filter. The recovered material was dried under vacuum at a temperature of 40° C. for 12 hours, thereby obtaining 0.37 g (32% yield) of poly(t-butyl 3α-(5-norbornene-2-carbonyloxy)-7α, 12α-dihydroxy-5β-cholan-24-oate-maleic anhydride), as a white solid.

Workup

  1. additionThe solution was introduced into a polymerization glass tube ampule which
  2. customwas then sealed under vacuum
  3. customThen, the solution was polymerized at a temperature of 65° C. for 20 hours
  4. customAfter the polymerization
  5. customthe polymerization product was precipitated in petroleum ether/ethyl ether(5/1, volume ratio)
  6. customthe precipitate was recovered with a glass
  7. filtrationfilter
  8. customThe recovered material was dried under vacuum at a temperature of 40° C. for 12 hours

Sources & evidence

ORD record
ord-2f1015dfb2a64b0d94e158d22db25c15
Source dataset
uspto-grants-2001_07
Patent number
US06258508B1

Reaction notes

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