Acetyl chloride → (R/S)-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetic acid

HRID 1906276Notes

Reaction equation

HRID 1906276 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]([OH:10])=[O:9])[C:3]1=[O:11].[C:12](Cl)(=[O:14])[CH3:13]>O1CCCC1>[C:12]([O:1][CH:2]1[CH2:6][CH2:5][N:4]([CH2:7][C:8]([OH:10])=[O:9])[C:3]1=[O:11])(=[O:14])[CH3:13]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 19817647(R/S)-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetic acid

Product 1

HCID 54389912(R/S)-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.0 g of (R/S)-2-(3-hydroxy-2-oxo-1-pyrrolidinyl)acetic acid, 80 ml of absolute tetrahydrofuran and 5 ml of acetyl chloride are boiled at reflux for 4 hours while stirring. Thereafter, the mixture is evaporated. The residue is filtered through silica gel (granular size 0.2-0.5 mm). The evaporation residue of the fractions which are eluted with ethyl acetate is stirred in diethyl ether. By filtration there is isolated (R/S)-2-(3-acetoxy-2-oxo-1-pyrrolidinyl)acetic acid of melting point 95°-96°.

Workup

  1. temperatureat reflux for 4 hours
  2. customThereafter, the mixture is evaporated
  3. filtrationThe residue is filtered through silica gel (granular size 0.2-0.5 mm)
  4. washThe evaporation residue of the fractions which are eluted with ethyl acetate
  5. stirringis stirred in diethyl ether
  6. filtrationBy filtration

Sources & evidence

ORD record
ord-f1340adf623b4dadac8a978d029ab879
Source dataset
uspto-grants-1987_03
Patent number
US04650878

Reaction notes

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