Triethylamine → 1-(2-Nitrophenyl)-L-proline

HRID 1976218Notes

Reaction equation

HRID 1976218 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].F[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17].C(N(CC)CC)C>CS(C)=O>[N+:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 738951-Fluoro-2-nitrobenzeneHCID 145742L-Proline

Product 1

HCID 281193991-(2-Nitrophenyl)-L-prolineYield 80.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

There were dissolved, in 25 ml of dimethyl sulfoxide, 1 g of L-proline and 1.23 g of 1-fluoro-2-nitrobenzene, then 1.65 ml of triethylamine was added to the resulting solution and the mixture was stirred with heating at 60° C. for 16 hours. The reaction solution was cooled to room temperature then poured into ice water and washed with ether. The aqueous phase was acidified with hydrochloric acid and extracted with ether. After washing the organic phase with water, the phase was dried over anhydrous magnesium sulfate and then concentrated. The resulting residue was treated by silica gel column chromatography, followed by elution with methanol/chloroform (1/49) to give 1.65 g (yield: 80.3%) of the title compound.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. washwashed with ether
  3. extractionextracted with ether
  4. washAfter washing the organic phase with water
  5. dry with materialthe phase was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. additionThe resulting residue was treated by silica gel column chromatography
  8. washfollowed by elution with methanol/chloroform (1/49)

Sources & evidence

ORD record
ord-5a69916ec12d4ce0ab39633c7fb8e452
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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