HCID 53975417, compound → HCID 20622763, compound

HRID 2121219Notes

Reaction equation

HRID 2121219 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C@H:4]([CH2:28][CH2:29][S:30][CH3:31])[NH:5][C:6](=[O:27])[C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[CH:9][C:8]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26]>CO.[Pd]>[CH3:1][O:2][C:3](=[O:32])[C@H:4]([CH2:28][CH2:29][S:30][CH3:31])[NH:5][C:6](=[O:27])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)=[CH:9][C:8]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH3:26]

Participants

4

Reactant 1

HCID 53975417HCID 53975417, compound

Product 1

HCID 20622763HCID 20622763, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of the product of Example 278A (171 mg, 0.38 mmol) and palladium (10%) on carbon (489 mg, 0.46 mmol of palladium) in methanol was flushed with hydrogen, and stirred under a hydrogen balloon for 5 hours. The mixture was then filtered through Celite, rinsed, with ethyl acetate, and concentrated in vacuo. The residue was purified by column chromatography (5% methanol-ethyl acetate) to give the title compound (97 mg, 56%).

Workup

  1. customwas flushed with hydrogen
  2. filtrationThe mixture was then filtered through Celite
  3. washrinsed, with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (5% methanol-ethyl acetate)

Sources & evidence

ORD record
ord-2868ea8b8b59402d89f1915ad556810c
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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