L-Hydroxyproline → HCID 2755917, compound

HRID 1976228Notes

Reaction equation

HRID 1976228 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6][C:5](=[O:12])[O:4][C:2]2=O.[OH:13][C@H:14]1[CH2:18][NH:17][C@H:16](C(O)=O)[CH2:15]1>CS(C)=O>[OH:13][C@H:14]1[CH2:18][N:17]2[C@H:16]([C:5](=[O:12])[NH:6][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=3[C:2]2=[O:4])[CH2:15]1

Participants

4

Reactant 2

HCID 5810L-HydroxyprolineHCID 8359Isatoic Anhydride

Product 1

HCID 2755917HCID 2755917, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

Isatoic anhydride (3.5 g) and trans-4-hydroxy-L-proline (2.8 g) were suspended in 60 ml of dimethyl sulfoxide and the suspension was heated with stirring at 120° C. for 2 hours. After allowing the reaction liquid to cool, the solvent was distilled off under reduced pressure and the resulting residue was washed with ethyl acetate and dried. The crude crystals were recrystallized from ethanol to give 3.9 g (yield 78.5%) of the title compound.

Workup

  1. temperaturethe suspension was heated
  2. customthe reaction liquid
  3. temperatureto cool
  4. distillationthe solvent was distilled off under reduced pressure
  5. washthe resulting residue was washed with ethyl acetate
  6. customdried
  7. customThe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-38fd80e6961c406997a8d9258b3f9be6
Source dataset
uspto-grants-2001_05
Patent number
US06225306B1

Reaction notes

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