N-benzylsulfonyl-D-leucyl-L-proline benzyl ester → N-benzylsulfonyl-D-leucyl-L-proline

HRID 58033Notes

Reaction equation

HRID 58033 reaction equation
C([O:8][C:9](=[O:33])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:32])[C@@H:16]([CH2:28][CH:29]([CH3:31])[CH3:30])[NH:17][S:18]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:20])=[O:19])C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[CH2:21]([S:18]([NH:17][C@@H:16]([C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([OH:33])=[O:8])=[O:32])[CH2:28][CH:29]([CH3:31])[CH3:30])(=[O:20])=[O:19])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 86700987N-benzylsulfonyl-D-leucyl-L-proline benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 86700986N-benzylsulfonyl-D-leucyl-L-prolineYield 101%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

N-benzylsulfonyl-D-leucyl-L-proline benzyl ester (1.2 g) was dissolved in methanol (20 ml), and 10% palladium-carbon (120 mg) was added. The resulting mixture aerated with hydrogen was allowed to react at room temperature for 3 h, filtered and concentrated under reduced pressure to remove the solvent to give a white foam-like solid (981 mg, 97%), which was directly used for the next reaction.

Workup

  1. customto react at room temperature for 3 h
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customto remove the solvent

Sources & evidence

ORD record
ord-7e77bde1d3014cba9288af4519cee80b
Source dataset
uspto-grants-2016_09
Patent number
US09434760B2

Reaction notes

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