HCID 53906143, compound → HCID 53884142, compound

HRID 1871706Notes

Reaction equation

HRID 1871706 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:36])[CH2:17][CH2:18][C:19]([N:21]1[CH2:25][CH2:24][CH2:23][C@@H:22]1[C:26]([O:28]CC1C=CC=CC=1)=[O:27])=[O:20])=[O:10])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[C:26]([C@H:22]1[CH2:23][CH2:24][CH2:25][N:21]1[C:19](=[O:20])[CH2:18][CH2:17][C:16]([N:12]1[CH2:13][CH2:14][CH2:15][C@@H:11]1[C:9]([OH:10])=[O:8])=[O:36])([OH:28])=[O:27]

Participants

5

Reactant 2

HCID 53906143HCID 53906143, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53884142HCID 53884142, compoundYield 108.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 256 mg (0.5 mmol) (R)-1-[4-[(R)-2-benzyloxycarbonyl-pyrrolidin -1-yl]-4-oxo-butyryl]-pyrrolidine-2-carboxylic acid benzyl ester in 5 ml ethanol as stirred with 13 mg 10% Palladium on carbon under 1 atm of hydrogen for 16 h at room temperature. After filtration to remove the catalyst, concentration in vacuo afforded 170 mg (100%) of the title compound (R)-1- [4-[(R)-2-carboxy-pyrrolidin-1-yl]-4-oxo-butyryl]-pyrrolidine-2-carboxylic acid as a colorless viscous oil. MS m/e (%): 313 (M+H)+, 100).

Workup

  1. filtrationAfter filtration
  2. customto remove
  3. concentrationthe catalyst, concentration in vacuo

Sources & evidence

ORD record
ord-adf6d518c40e44ab9d3fca6deb1508a7
Source dataset
uspto-grants-2000_08
Patent number
US06103910

Reaction notes

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