L-Hydroxyproline → 4-Hydroxy-1-(4-nitrophenyl)pyrrolidine-2-carboxylic acid

HRID 719741Notes

Reaction equation

HRID 719741 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[OH:17][C@H:18]1[CH2:22][NH:21][C@H:20]([C:23]([OH:25])=[O:24])[CH2:19]1>O>[OH:17][CH:18]1[CH2:22][N:21]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH:20]([C:23]([OH:25])=[O:24])[CH2:19]1

Participants

5

Reactant 3

HCID 5810L-HydroxyprolineHCID 9590p-FluoronitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 219018724-Hydroxy-1-(4-nitrophenyl)pyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

10 g (70.9 mmol) of 4-fluoronitrobenzene, 11.75 g (85 mmol) of potassium carbonate and 9.3 g (70.8 mmol) of trans-4-hydroxyproline were stirred in 100 ml of distilled water. The mixture was refluxed for 16 hours and was then cooled to room temperature. The product was extracted with ethyl acetate. The organic phases were washed with a saturated solution, dried over sodium sulphate and concentrated under reduced pressure. The oil obtained was crystallized from an ethyl acetate/heptane mixture. A yellow powder was obtained.

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. extractionThe product was extracted with ethyl acetate
  3. washThe organic phases were washed with a saturated solution
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe oil obtained
  7. customwas crystallized from an ethyl acetate/heptane mixture
  8. customA yellow powder was obtained

Sources & evidence

ORD record
ord-16dbd8d3185e4f769d97466d0c90dbad
Source dataset
uspto-grants-2006_11
Patent number
US07132543B2

Reaction notes

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