Water → Benzyloxycarbonyl-L-proline

HRID 1186005Notes

Reaction equation

HRID 1186005 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([OH:8])=[O:7].O.C([O-])([O-])=O.[Na+].[Na+].[CH:16]1[CH:21]=[CH:20][C:19]([CH2:22][O:23][C:24](Cl)=[O:25])=[CH:18][CH:17]=1>C1COCC1>[CH2:22]([O:23][C:24]([N:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([OH:8])=[O:7])=[O:25])[C:19]1[CH:20]=[CH:21][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 145742L-Proline

Product 1

HCID 101987Benzyloxycarbonyl-L-prolineYield 69.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-pyrrolidine-2-carboxylic acid (7) (2.0 g, 17.39 mmol) in THF:H2O (20 mL, 1:1) were added Na2CO3 (2.76 g, 26.08 mmol) and Cbz-Cl (3.54 g, 20.80 mmol) and stirred at RT for 18 h. The reaction mixture was washed with EtOAc (10 mL) and the aqueous layer was acidified with 3N HCl and extracted with EtOAc (2×20 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to yield compound 8 (3.0 g, 69.7%).

Workup

  1. washThe reaction mixture was washed with EtOAc (10 mL)
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-115a069eb68846daa8a272ce9a33e0e8
Source dataset
uspto-grants-2014_03
Patent number
US08673843B2

Reaction notes

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