Glutaric anhydride → Pentanoic acid, 5-[(2,5-dioxo-1-pyrrolidinyl)oxy]-5-oxo-
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
Product 1
Reagents, catalysts & solvents 1
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.