HCID 69062805, compound → HCID 69058133, compound

HRID 2099135Notes

Reaction equation

HRID 2099135 reaction equation
[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[C:3]=1[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][C@:7]1([CH3:14])[C:11]([OH:13])=[O:12])=[O:5].[H][H]>CO.[Pd]>[NH2:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[C:3]=1[C:4]([N:6]1[CH2:10][CH2:9][CH2:8][C@:7]1([CH3:14])[C:11]([OH:13])=[O:12])=[O:5]

Participants

5

Reactant 2

HCID 69062805HCID 69062805, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69058133HCID 69058133, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

366 mg (1.25 mmol) (R)-1-(2-amino-6-nitro-benzoyl)-2-methyl-pyrrolidine-2-carboxylic acid are dissolved in 50 mL methanol and combined with 40 mg palladium on charcoal (10% Pd). The reaction mixture is hydrogenated for 9 h at 5 bar hydrogen pressure and at 25° C. Then the catalyst is filtered off, the solvent is eliminated in vacuo and the crude product is purified by chromatography. The carrier material used is C18-RP-silica gel and a gradient is run through which consists of 95% water and 5% acetonitrile at the starting point and 5% water and 95% acetonitrile at the end point.

Workup

  1. filtrationThen the catalyst is filtered off
  2. customthe crude product is purified by chromatography

Sources & evidence

ORD record
ord-ab249cdb8a0f4d74bddea77bb6864c7e
Source dataset
uspto-grants-2009_08
Patent number
US07569561B2

Reaction notes

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