Pyridine → HCID 131714192, compound

HRID 1981231Notes

Reaction equation

HRID 1981231 reaction equation
[CH3:1][C@@H:2]([C@@H:7]1[C@@H:11]2[CH2:12][CH2:13][C@@:14]3([CH3:32])[C@:19]4([CH3:31])[CH2:20][CH2:21][C@H:22]5[C:27]([CH3:29])([CH3:28])[CH2:26][CH2:25][CH2:24][C@:23]5([CH3:30])[C@H:18]4[CH2:17][CH2:16][C@@H:15]3[C@@:10]2([CH3:33])[CH2:9][CH2:8]1)[CH2:3][CH2:4][CH2:5][OH:6].[N:34]1C=CC=CC=1.C(N(CC)CC)C.[C:47](Cl)(=[O:51])[C:48]([CH3:50])=[CH2:49]>ClCCl.C(OCC)C>[C:47]([NH2:34])(=[O:51])[C:48]([CH3:50])=[CH2:49].[CH3:1][C@@H:2]([C@@H:7]1[C@@H:11]2[CH2:12][CH2:13][C@@:14]3([CH3:32])[C@:19]4([CH3:31])[CH2:20][CH2:21][C@H:22]5[C:27]([CH3:29])([CH3:28])[CH2:26][CH2:25][CH2:24][C@:23]5([CH3:30])[C@H:18]4[CH2:17][CH2:16][C@@H:15]3[C@@:10]2([CH3:33])[CH2:9][CH2:8]1)[CH2:3][CH2:4][CH2:5][OH:6]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 162967bacteriohopane-32-ol

Product 1

HCID 131714192HCID 131714192, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Into a one-liter, 3-neck flask equipped with a reflux condenser, a pressure equalizing addition funnel and a magnetic stirrer are charged 200 g (0.07 mole) of Monol I, 22 g (0.28 mole) of pyridine and 200 ml of anhydrous diethyl ether. Under a static nitrogen purge with cooling to ~2° C., 14.4 g of toluene sulfonyl chloride dissolved in 25 ml of diethyl ether is added with stirring over a period of one half of an hour. The reaction mixture is allowed to warm to room temperature and stirred for 12 hours. Thereafter, the diethyl ether is removed under reduced pressure at temperatures less than 40° C. The reaction mixture is filtered to remove pyridine hydrochloride and then charged into a one-liter, 3-neck flask equipped with a reflux condenser, gas sparge addition tube and a magnetic stirrer. To this flask is added with stirring 200 ml of dichloromethane and anhydrous ammonia is sparged through the reaction mixture for 11/2 hours followed by sparging with nitrogen for 2 hours. The reaction mixture is filtered and then subjected to reduced pressure to remove dichloromethane. Into the aforementioned flask are added the reaction product, 200 ml of dichloromethane and 7.0 g (0.07 mole) of triethylamine. To the resulting solution is added with stirring and refluxing, 7.9 g (0.075 mole) of methacryloyl chloride diluted in 25 ml of dichloromethane over a period of 30 minutes and stirred overnight. The resulting product is cooled and subjected to reduced pressure to remove dichloromethane. To this product is added 200 ml of diethyl ether, then filtered and subjected to reduced pressure to remove diethyl ether thereby providing the aforementioned desired adduct.

Workup

  1. customInto a one-liter, 3-neck flask equipped with a reflux condenser
  2. additionaddition funnel and a magnetic stirrer
  3. customUnder a static nitrogen purge
  4. temperaturewith cooling to ~2° C.
  5. dissolution14.4 g of toluene sulfonyl chloride dissolved in 25 ml of diethyl ether
  6. additionis added
  7. stirringstirred for 12 hours
  8. customThereafter, the diethyl ether is removed under reduced pressure at temperatures less than 40° C
  9. filtrationThe reaction mixture is filtered
  10. customto remove pyridine hydrochloride
  11. additioncharged into a one-liter, 3-neck flask
  12. customequipped with a reflux condenser
  13. customgas sparge
  14. additionaddition tube and a magnetic stirrer
  15. additionTo this flask is added
  16. stirringwith stirring 200 ml of dichloromethane and anhydrous ammonia
  17. customis sparged through the reaction mixture for 11/2 hours
  18. customby sparging with nitrogen for 2 hours
  19. filtrationThe reaction mixture is filtered
  20. customto remove dichloromethane
  21. additionTo the resulting solution is added
  22. stirringwith stirring
  23. temperaturerefluxing
  24. stirringstirred overnight
  25. temperatureThe resulting product is cooled
  26. customto remove dichloromethane
  27. additionTo this product is added 200 ml of diethyl ether
  28. filtrationfiltered
  29. customto remove diethyl ether

Sources & evidence

ORD record
ord-de85989a4f7f4f2abf94ee5ea6ee8a34
Source dataset
uspto-grants-1985_04
Patent number
US04513124

Reaction notes

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