HCID 44351848, compound → HCID 54514540, compound

HRID 1780518Notes

Reaction equation

HRID 1780518 reaction equation
[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:24])([C:7]3[CH:15]=[CH:14][C:13]([C:16]#[C:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:25].[H][H]>[Pd].N1C=CC=CC=1>[CH3:1][N:2]1[C@H:11]2[C@@:6]([CH3:24])([C:7]3[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:12][C:8]=3[CH2:9][CH2:10]2)[CH2:5][CH2:4][C:3]1=[O:25]

Participants

5

Reactant 2

HCID 44351848HCID 44351848, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54514540HCID 54514540, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049PyridineSolvent

Procedure

A 300 mg portion of the product of Example 284 was hydrogenated over palladium/barium sulfate catalyst in 25 mL of pyridine at 15 psi hydrogen pressure at ambient temperature for 1 h. The mixture was then filtered and concentrated under vacuum, and the residue was purified by chromatography on silica gel, eluting with 75% ethyl acetate/hexane. The product thereby obtained was further purified on a Chromatatron, eluting with 5% isopropanol in chloroform to obtain the desired product in the form of a yellow oil. High resolution mass spectroscopy showed the correct molecular ion of 332.201440.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated under vacuum
  3. customthe residue was purified by chromatography on silica gel
  4. washeluting with 75% ethyl acetate/hexane
  5. customThe product thereby obtained
  6. customwas further purified on a Chromatatron
  7. washeluting with 5% isopropanol in chloroform

Sources & evidence

ORD record
ord-b00303346e2e4db4947884f2105462e5
Source dataset
uspto-grants-1997_05
Patent number
US05629007

Reaction notes

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