HCID 86700990, compound → N-benzenesulfonyl-D-leucyl-(S)-azetidine-2-carboxylic acid

HRID 58034Notes

Reaction equation

HRID 58034 reaction equation
C([O:8][C:9]([C@@H:11]1[CH2:14][CH2:13][N:12]1[C:15](=[O:31])[C@@H:16]([CH2:27][CH:28]([CH3:30])[CH3:29])[NH:17][S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])=[O:10])C1C=CC=CC=1.[H][H]>CO.[C].[Pd]>[C:21]1([S:18]([NH:17][C@@H:16]([C:15]([N:12]2[CH2:13][CH2:14][C@H:11]2[C:9]([OH:10])=[O:8])=[O:31])[CH2:27][CH:28]([CH3:30])[CH3:29])(=[O:20])=[O:19])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 86700990HCID 86700990, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86700989N-benzenesulfonyl-D-leucyl-(S)-azetidine-2-carboxylic acidYield 99%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

N-benzenesulfonyl-D-leucyl-(S)-azetidine-2-carboxylic acid benzyl ester (667 mg) was dissolved in methanol (10 ml), and 10% palladium-carbon (80 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 (520 mg, 99%), 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-2386088e0d594ce9b04ac6f410532032
Source dataset
uspto-grants-2016_09
Patent number
US09434760B2

Reaction notes

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