HCID 178418853, compound → HCID 178418966, compound

HRID 10518Notes

Reaction equation

HRID 10518 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]=[N+]=[N-])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:10][CH2:11][C@H:12]([NH2:15])[CH2:13][CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 178418853HCID 178418853, compound

Product 1

HCID 178418966HCID 178418966, compoundYield 36.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The roughly purified product of Intermediate 37 (142 g) was reduced by hydrogenation at room temperature for 9 hours by using 10% Pd/C (7.1 g) and ethyl acetate solution (1.42 l) under hydrogen atmosphere of 1 atm. The palladium catalyst was removed by filtration, and the solvent was evaporated under reduced pressure. Then, the residue was purified by flash column chromatography (chloroform:methanol:triethylamine=100:20:10) to obtain the title compound (45.8 g).

Workup

  1. customThe palladium catalyst was removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThen, the residue was purified by flash column chromatography (chloroform:methanol:triethylamine=100:20:10)

Sources & evidence

ORD record
ord-fea9acd2f75549b088952fd82f2bc28a
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Reaction notes

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