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

HRID 1795745Notes

Reaction equation

HRID 1795745 reaction equation
[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]

Participants

4

Reactant 2

HCID 7940Glutaric anhydrideHCID 80170N-Hydroxysuccinimide

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-258c6b900bdb40c59fdf2610625fcb97
Source dataset
uspto-grants-2006_04
Patent number
US07029918B2

Reaction notes

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