تفاعل #1361226

معادلة التفاعل

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

acetic anhydride

phenothiazine

HCl

water

→

desired product

N-Succinimidyl 6-Maleimidohexanoate

المذيبات

THF

Triethylamine

ظروف التفاعل

المعالجة

1. 1
   أخرىequipped with an overhead stirrer
2. 2
   درجة الحرارةthe mixture was heated
3. 3
   درجة الحرارةto reflux
4. 4
   درجة الحرارةAfter a total of 4 hours of reflux
5. 5
   درجة الحرارةthe dark mixture was cooled to <60° C.
6. 6
   workup.STIRRINGThe mixture was stirred 3 hours at room temperature
7. 7
   ترشيحwas filtered through a Celite 545 pad
8. 8
   أخرىto remove solids
9. 9
   استخلاصThe filtrate was extracted with 4×500 ml of chloroform
10. 10
    تجفيفthe combined extracts were dried over sodium sulfate
11. 11
    workup.ADDITIONAfter adding 15 mg of phenothiazine
12. 12
    أخرىpolymerization
13. 13
    أخرىthe solvent was removed under reduced pressure
14. 14
    أخرىThe 6-maleimidohexanoic acid was recrystallized from hexane/chloroform (2/1)
15. 15
    أخرىto give typical
16. 16
    أخرىyields of 76-83 g (55-60%) with a melting point of 81-85° C

الإجراء التجريبي

(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.

المصدر