(R)-1-[3-[[3-[(R)-2-benzyloxycarbonyl-pyrrolidin-1-yl]-3-oxo-propyl]-propyl-amino]-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester → (R)-1-[3-[[3-[(R)-2-Carboxy-pyrrolidin-1-yl]-3-oxo-propyl]-propyl-amino]-propionyl]-pyrrolidine-2-carboxylic acid

HRID 1636106Notes

Reaction equation

HRID 1636106 reaction equation
C([O:8][C:9]([C@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16](=[O:42])[CH2:17][CH2:18][N:19]([CH2:23][CH2:24][C:25]([N:27]1[CH2:31][CH2:30][CH2:29][C@@H:28]1[C:32]([O:34]CC1C=CC=CC=1)=[O:33])=[O:26])[CH2:20][CH2:21][CH3:22])=[O:10])C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[C:32]([C@H:28]1[CH2:29][CH2:30][CH2:31][N:27]1[C:25](=[O:26])[CH2:24][CH2:23][N:19]([CH2:20][CH2:21][CH3:22])[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:42])([OH:34])=[O:33]

Participants

5

Reactant 2

HCID 54362609(R)-1-[3-[[3-[(R)-2-benzyloxycarbonyl-pyrrolidin-1-yl]-3-oxo-propyl]-propyl-amino]-propionyl]-pyrrolidine-2-carboxylic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 54332800(R)-1-[3-[[3-[(R)-2-Carboxy-pyrrolidin-1-yl]-3-oxo-propyl]-propyl-amino]-propionyl]-pyrrolidine-2-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 84 mg (0.15 mmol) (R)-1-[3-[[3-[(R)-2-benzyloxycarbonyl-pyrrolidin-1-yl]-3-oxo-propyl]-propyl-amino]-propionyl]-pyrrolidine-2-carboxylic acid benzyl ester in 3 ml ethanol was stirred with 10 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 58 mg (100%) of the title compound (R)-1-[3-[[3-[(R)-2-carboxy-pyrrolidin-1-yl]-3-oxo-propyl]-propylamino]-propionyl]-pyrrolidine-2-carboxylic acid as a white solid.

Workup

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

Sources & evidence

ORD record
ord-30be3ada5e6e4f0a8dd2fa558ef9ff0b
Source dataset
uspto-grants-2003_01
Patent number
US06512001B1

Reaction notes

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