HCID 86594360, compound → HCID 69034585, compound

HRID 351366Notes

Reaction equation

HRID 351366 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C@H:8]1[CH2:12][CH2:11][N:10]([C@H:13]2[CH2:18][CH2:17][C@@H:16]([N:19]=[N+]=[N-])[CH2:15][C@H:14]2[CH2:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([S:32][CH3:33])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[C:9]1=[O:34])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd].[O-]S([O-])(=O)=O.[Ba+2]>[C:1]([O:5][C:6](=[O:35])[NH:7][C@H:8]1[CH2:12][CH2:11][N:10]([C@H:13]2[CH2:18][CH2:17][C@@H:16]([NH2:19])[CH2:15][C@H:14]2[CH2:22][S:23]([C:26]2[CH:31]=[CH:30][C:29]([S:32][CH3:33])=[CH:28][CH:27]=2)(=[O:25])=[O:24])[C:9]1=[O:34])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 86594360HCID 86594360, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69034585HCID 69034585, compoundYield 149.4%

Reagents, catalysts & solvents 2

HCID 16218511Pd barium sulfateCatalystHCID 887MethanolSolvent

Procedure

{(3S)-1-[(1S,2R,4R)-4-Azido-2-(4-methylsulfanyl-benzenesulfonylmethyl)-cyclohexyl]-2-oxo-pyrrolidin-3-yl}-carbamic acid tert-butyl ester (350 mg), from the synthesis of Example 17 (analogous to 10f), was dissolved in MeOH (5 mL) prior to the addition of 5% Pd/BaSO4 (300 mg). A hydrogen balloon was added and the mixture was stirred. After stirring 1 h, the Pd/BaSO4 was filtered off and the solvent was concentrated to give {(3S)-1-[(1S,2R,4R)-4-amino-2-(4-methylsulfanyl-benzenesulfonylmethyl)-cyclohexyl]-2-oxo-pyrrolidin-3-yl}-carbamic acid tert-butyl ester (497 mg). MS found: (M−H)−=496.5.

Workup

  1. stirringAfter stirring 1 h
  2. filtrationthe Pd/BaSO4 was filtered off
  3. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-a1b39d0950734da4b58445e62040c5fc
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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