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

HRID 1016667Notes

Reaction equation

HRID 1016667 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 The reaction
  3. concentrationwas concentrated at reduced pressure to an oil
  4. customThe oil was crystallized from 50 mL of ethyl acetate

Sources & evidence

ORD record
ord-0288383743c74ee5bca963f1116956dc
Source dataset
uspto-grants-2002_11
Patent number
US06476199B1

Reaction notes

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