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

HRID 1108005Notes

Reaction equation

HRID 1108005 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 46.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 10.0 g (0.088 mol) of glutaric anhydride in 50 mL of dry THF under argon was treated with 10.0 g (0.087 mol) of N-hydroxysuccinimide and heated to reflux for 3.5 hours. The reaction was concentrated at reduced pressure to an oil. The oil was crystallized from 50 mL of ethyl acetate to yield 9.2 g (46%) of 5-[(2,5-dioxo-1-pyrrolidinyl)oxy]-5-oxo-pentanoic acid which was treated with 16 mL of thionyl chloride and heated at 45° C. for 3 hours under argon. The reaction mixture was concentrated at reduced pressure to a white solid which was triturated with a small amount of ether and collected by suction filtration. The product was dried overnight at high vacuum to yield 8.7 g (88%) of 18 as a white solid.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3.5 hours
  3. concentrationThe reaction was concentrated at reduced pressure to an oil
  4. customThe oil was crystallized from 50 mL of ethyl acetate

Sources & evidence

ORD record
ord-5d42c78ec61545bb9b26e67c4d2682e4
Source dataset
uspto-grants-2000_05
Patent number
US06063908

Reaction notes

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