Dicyclohexylcarbodiimide → 1-{2-[(2,5-Dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}-1H-pyrrole-2,5-dione

HRID 327358

Reaction equation

HRID 327358 reaction equation
[C:1]1(=[O:11])[N:5]([CH2:6][C:7]([OH:9])=[O:8])[C:4](=[O:10])[CH:3]=[CH:2]1.O[N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19].C1(N=C=NC2CCCCC2)CCCCC1>COCCOCCOC>[CH2:16]1[C:17](=[O:18])[N:13]([O:8][C:7]([CH2:6][N:5]2[C:4](=[O:10])[CH:3]=[CH:2][C:1]2=[O:11])=[O:9])[C:14](=[O:19])[CH2:15]1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 3199352-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)acetic acid

Product 1

HCID 32992291-{2-[(2,5-Dioxopyrrolidin-1-yl)oxy]-2-oxoethyl}-1H-pyrrole-2,5-dioneYield 99.1%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

Maleimidoacetic acid (155 mg, 1.0 mmol) in 5 ml of diglyme was treated at 0° C. with N-hydroxysuccinimide (127 mg, 1.1 mmol) and dicyclohexylcarbodiimide (227 mg, 1.1 mmol). After 1 hour at 0° C. and 3 hours at room temperature, the reaction mixture was filtered and evaporated to dryness to yield 0.25 g of crude maleimidoacetic acid N-succinimidyl ester.

Workup

  1. filtration3 hours at room temperature, the reaction mixture was filtered
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-af1dc5f34405494aaf454788d0f1a090
Source dataset
uspto-grants-1993_12
Patent number
US05273743

Linked notes

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