Triethylamine → Methyl 4-[(2,5-dioxopyrrolidin-1-yl)oxy]-4-oxobutanoate

HRID 624548Notes

Reaction equation

HRID 624548 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[CH3:9][O:10][C:11](=[O:17])[CH2:12][CH2:13][C:14](Cl)=[O:15].C(N(CC)CC)C>C(OCC)(=O)C>[CH3:9][O:10][C:11](=[O:17])[CH2:12][CH2:13][C:14]([O:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 80170N-Hydroxysuccinimide

Product 1

HCID 13798889Methyl 4-[(2,5-dioxopyrrolidin-1-yl)oxy]-4-oxobutanoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-hydroxy-pyrrolidine-2,5-dione (1.23 mL, 10 mmol) in ethyl acetate (50 mL) was added 3-chlorocarbonyl-propionic acid methyl ester (1.15 g, 10 mmol). The mixture was cooled in an ice bath. Triethylamine (1.4 mL, 10 mmol) was added dropwise. The resulting suspension was stirred for 10 min in an ice bath and for 5 min without ice bath. The white solid was removed by filtration and washed with ethyl acetate (3×3 mL). The filtrate was concentrated to a white solid (2.32 g).

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customThe white solid was removed by filtration
  3. washwashed with ethyl acetate (3×3 mL)
  4. concentrationThe filtrate was concentrated to a white solid (2.32 g)

Sources & evidence

ORD record
ord-fa6b295db93f4431a384e23a204b532d
Source dataset
uspto-grants-2016_04
Patent number
US09303041B2

Reaction notes

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