N-Hydroxyphthalimide → HCID 22119481, compound

HRID 1275369Notes

Reaction equation

HRID 1275369 reaction equation
[CH3:1][Si:2]([CH2:5][C:6]([OH:8])=O)([CH3:4])[CH3:3].O[N:10]1[C:14](=[O:15])[C:13]2=[CH:16][CH:17]=CC=[C:12]2[C:11]1=[O:20].C1C[O:24][CH2:23][CH2:22]1.O1CCOCC1>>[Si:2]([C:5]1[C:6]([O:8][C:23](=[O:24])[CH3:22])=[C:12]2[C:11](=[O:20])[NH:10][C:14](=[O:15])[C:13]2=[CH:16][CH:17]=1)([CH3:4])([CH3:3])[CH3:1]

Participants

4

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 75366Acetic acid, (trimethylsilyl)-HCID 22018518Dioxane tetrahydrofuran

Product 1

HCID 22119481HCID 22119481, compound

Procedure

Trimethylsilylacetic acid (0.1 mmole) and N-hydroxyphthalimide (0.1 mmole) were weighed under N2 and placed in a conical flask with 2 side arms (flask A). Dry THF/dioxane (0.5 mL) was added and removed carefully under vacuum to dry the substrates. THF (0.4 mL) was added and mixed to dissolve the substrates. DCC (95 μL, 1 M solution in methylene chloride) dried on activated molecular sieves was added and mixed. The reaction was stirred 3 hours, and a precipitate formed after 10 minutes. THF was removed under vacuum to dryness. Dry ether was added (1 mL) and mixed to dissolve the product of coupling, the reaction was left for 5 minutes for the by-product dicyclohexylurea to settle. The upper layer was transferred and filtered into the second flask. Dry ether (0.5 mL) was added, mixed and the upper layer was again transferred as above. The ether was removed under vacuum to leave the TMS-acetoxyphthalimide as a white solid.

Workup

  1. customplaced in a conical flask with 2 side arms
  2. customremoved carefully under vacuum
  3. customto dry the substrates
  4. additionTHF (0.4 mL) was added
  5. additionmixed
  6. dissolutionto dissolve the substrates
  7. dry with materialDCC (95 μL, 1 M solution in methylene chloride) dried on activated molecular sieves
  8. additionwas added
  9. additionmixed
  10. customa precipitate formed after 10 minutes
  11. customTHF was removed under vacuum to dryness
  12. additionDry ether was added (1 mL)
  13. additionmixed
  14. dissolutionto dissolve the product of coupling
  15. waitthe reaction was left for 5 minutes for the by-product dicyclohexylurea
  16. filtrationfiltered into the second flask
  17. additionDry ether (0.5 mL) was added
  18. additionmixed
  19. customThe ether was removed under vacuum

Sources & evidence

ORD record
ord-b85de4b312104b77bc8054c5c0224a1a
Source dataset
uspto-grants-2000_12
Patent number
US06160128

Reaction notes

Loading…