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Glutaric anhydride → Pentanoic acid, 5-[(2,5-dioxo-1-pyrrolidinyl)oxy]-5-oxo-

HRID 1795745
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HRID 1795745 반응식
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][CH2:3][CH2:2]1.[OH:9][N:10]1[C:14](=[O:15])[CH2:13][CH2:12][C:11]1=[O:16]>C1COCC1>[O:16]=[C:11]1[CH2:12][CH2:13][C:14](=[O:15])[N:10]1[O:9][C:1](=[O:8])[CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 7940Glutaric anhydrideHCID 80170N-Hydroxysuccinimide

생성물 1

HCID 9964613Pentanoic acid, 5-[(2,5-dioxo-1-pyrrolidinyl)oxy]-5-oxo-수율 79%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 10.0 g (0.0876 mole) of glutaric anhydride in 50 mL of THF was added 10.0 g (1 mole) of N-hydroxysuccinimide (NHS) and the reaction mixture boiled under reflux for 3.5 h. The resulting solution was concentrated under reduced pressure to an oil. The material was taken up in 50 mL of ethyl acetate and crystallization induced to yield a solid material which was filtered and washed with a little ethyl acetate to yield 15.8 g (79%) of 5-[(2,5-dioxo-1-pyrrolidinyl)oxy]-5-oxo-pentanoic acid. Re-crystallization from ethyl acetate and hexane afforded white needles. M.P.: 81–83° C. MA.

후처리

  1. temperatureunder reflux for 3.5 h
  2. concentrationThe resulting solution was concentrated under reduced pressure to an oil
  3. customcrystallization
  4. customto yield a solid material which
  5. filtrationwas filtered
  6. washwashed with a little ethyl acetate

출처 및 근거

ORD 기록
ord-258c6b900bdb40c59fdf2610625fcb97
출처 데이터셋
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07029918B2

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