Water → Benzyl 3-acetamido-4-oxopyrrolidine-1-carboxylate

HRID 400452Notes

Reaction equation

HRID 400452 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]([OH:16])[CH:13]([NH:17][C:18](=[O:20])[CH3:19])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.O>CS(C)=O.ClCCl>[C:18]([NH:17][CH:13]1[C:14](=[O:16])[CH2:15][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH2:12]1)(=[O:20])[CH3:19]

Participants

6

Reactant 3

HCID 962WaterHCID 81531DiisopropylethylamineHCID 86686049Benzyl 3-acetamido-4-hydroxypyrrolidine-1-carboxylate

Product 1

HCID 86686050Benzyl 3-acetamido-4-oxopyrrolidine-1-carboxylateYield 82.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

Pyidin-sulphur trioxide in 6.5 mL DMSO was added to 1.34 g benzyl-3-acetamido-4-hydroxypyrrolidine-1-carboxylate and 2.5 mL DIPEA in 8 mL dichlormethane at 0° C. The reaction was stirred 1 h at RT. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and sodium chloride solution and evaporated. The residue was purified by chromatography on silica gel (ethyl acetate) to give 1.1 g of the desired product. (M+H)+: 277

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and sodium chloride solution
  3. customevaporated
  4. customThe residue was purified by chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-e2e8a037eedd4e07991db0b07ec240a5
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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