L-Hydroxyproline → 1-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

HRID 1193501Notes

Reaction equation

HRID 1193501 reaction equation
[OH:1][C@H:2]1[CH2:6][NH:5][C@H:4]([C:7]([OH:9])=[O:8])[CH2:3]1.[CH2:10]([O:17][C:18](Cl)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[OH-].[Na+]>[CH2:10]([O:17][C:18]([N:5]1[CH2:6][C@H:2]([OH:1])[CH2:3][C@H:4]1[C:7]([OH:9])=[O:8])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 5810L-HydroxyprolineHCID 10387Benzyl chloroformate

Product 1

HCID 3915171-(Phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Trans-4-hydroxy-L-proline (4.7 g) was dissolved in 2N sodium hydroxide (36 ml), to which benzyloxycarbonylchloride (6.1 g) was slowly added dropwise under cooling with ice water. The mixture was then stirred at room temperature throughout a whole day and night. After the reaction, the mixture was washed with ethyl acetate, and to the aqueous layer was then added sodium chloride to saturation. Then the pH was adjusted to around 3 with 10N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated solution of sodium chloride in water and it was then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure whereby the titled compound (6.9 g) was obtained.

Workup

  1. additionwas slowly added dropwise
  2. customAfter the reaction
  3. washthe mixture was washed with ethyl acetate
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated solution of sodium chloride in water and it
  6. dry with materialwas then dried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure whereby the titled compound (6.9 g)
  8. customwas obtained

Sources & evidence

ORD record
ord-e6a1618ac31e40e8825d8f09e1a79422
Source dataset
uspto-grants-1989_03
Patent number
US04810721

Reaction notes

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