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

HRID 2371384Notes

Reaction equation

HRID 2371384 reaction equation
C(=O)(O)[O-].[Na+].[OH:6][C@H:7]1[CH2:11][NH:10][C@H:9]([C:12]([OH:14])=[O:13])[CH2:8]1.[CH2:15]([O:22][C:23](Cl)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O.C1(C)C=CC=CC=1>[CH2:15]([O:22][C:23]([N:10]1[CH2:11][C@H:7]([OH:6])[CH2:8][C@H:9]1[C:12]([OH:14])=[O:13])=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 5810L-HydroxyprolineHCID 10387Benzyl chloroformate2×HCID 516892Sodium Bicarbonate2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
28 °C

Procedure

Sodium bicarbonate (131.04 g) was dissolved in water (1040 ml), and trans-4-hydroxy-L-proline (78.6 g) was added thereto. To the resultant mixture, a solution of benzyloxycarbonyl chloride (72 ml) in dry toluene (320 ml) was added, and the mixture was stirred at an inner temperature of 28° C. for 3 hours. Sodium bicarbonate (65.52 g) and benzyloxycarbonyl chloride (72 ml) were additionally added thereto, and stirring was continued at the same temperature for 2 hours. The reaction mixture was washed with ether, and the aqueous layer was filtered. The filtrate was washed again with ether. The aqueous layer was adjusted to pH 1 with 6N hydrochloric acid and extracted with ethyl acetate. The extract was washed with aqueous sodium chloride solution, dried over sodium sulfate and concentrated to remove the solvent to give trans-1-benzyloxycarbonyl-4-hydroxy-L-proline.

Workup

  1. stirringstirring
  2. waitwas continued at the same temperature for 2 hours
  3. washThe reaction mixture was washed with ether
  4. filtrationthe aqueous layer was filtered
  5. washThe filtrate was washed again with ether
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with aqueous sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated
  10. customto remove the solvent

Sources & evidence

ORD record
ord-31394a1386604a9991ffca179aaac2ed
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

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