반응 #10217

반응 방정식

(Z)-4-Oxo-5-aza-2-undecendioic acid

acetic anhydride

phenothiazine

HCl

water

→

desired product

N-Succinimidyl 6-Maleimidohexanoate

용매

THF

Triethylamine

반응 조건

후처리

1. 1
   기타equipped with an overhead stirrer
2. 2
   온도the mixture was heated
3. 3
   온도to reflux
4. 4
   온도After a total of 4 hours of reflux
5. 5
   온도the dark mixture was cooled to <60° C.
6. 6
   workup.STIRRINGThe mixture was stirred 3 hours at room temperature
7. 7
   여과was filtered through a Celite 545 pad
8. 8
   기타to remove solids
9. 9
   추출The filtrate was extracted with 4×500 ml of chloroform
10. 10
    건조the combined extracts were dried over sodium sulfate
11. 11
    workup.ADDITIONAfter adding 15 mg of phenothiazine
12. 12
    기타polymerization
13. 13
    기타the solvent was removed under reduced pressure
14. 14
    기타The 6-maleimidohexanoic acid was recrystallized from hexane/chloroform (2/1)
15. 15
    기타to give typical
16. 16
    기타yields of 76–83 g (55–60%) with a melting point of 81–85° C

실험 절차

(Z)-4-Oxo-5-aza-2-undecendioic acid, 150.0 g (0.654 moles), acetic anhydride, 68 ml (73.5 g, 0.721 moles), and phenothiazine, 500 mg, were added to a 2 liter three-neck round bottom flask equipped with an overhead stirrer. Triethylamine, 91 ml (0.653 moles), and 600 ml of THF were added and the mixture was heated to reflux while stirring. After a total of 4 hours of reflux, the dark mixture was cooled to <60° C. and poured into a solution of 250 ml of 12 N HCl in 3 liters of water. The mixture was stirred 3 hours at room temperature and then was filtered through a Celite 545 pad to remove solids. The filtrate was extracted with 4×500 ml of chloroform and the combined extracts were dried over sodium sulfate. After adding 15 mg of phenothiazine to prevent polymerization, the solvent was removed under reduced pressure. The 6-maleimidohexanoic acid was recrystallized from hexane/chloroform (2/1) to give typical yields of 76–83 g (55–60%) with a melting point of 81–85° C. Analysis on a NMR spectrometer was consistent with the desired product.

출처