HCID 11174185, compound → HCID 11381223, compound

HRID 1295555Notes

Reaction equation

HRID 1295555 reaction equation
[CH3:1][C@@:2]1([OH:22])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[C:14]2[N:15]=[CH:16][N:17]=[C:18]([NH2:19])[C:13]=2[C:12]([C:20]#[CH:21])=[CH:11]1.[H][H]>C1COCC1.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[CH3:1][C@@:2]1([OH:22])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[C:14]2[N:15]=[CH:16][N:17]=[C:18]([NH2:19])[C:13]=2[C:12]([CH:20]=[CH2:21])=[CH:11]1

Participants

5

Reactant 2

HCID 11174185HCID 11174185, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11381223HCID 11381223, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The acetylene product prepared above was dissolved in 3 mL THF and 22 mg of Lindlar's catalyst was added. The solution was stirred at ambient temperature under 1 atm of hydrogen (via balloon) for 7 days. The balloon was recharged with hydrogen at the beginning of each day. After 7 days, the reaction was filtered through celite to remove catalyst, concentrated in vacuo, and purified by reverse phase HPLC on Phenominex column (250×20 mm) using a gradient of acetonitrile in water from 0 to 30% over 30 min at 10 mL/min to yield 30 mg (75% yield) of the title compound;

Workup

  1. filtrationthe reaction was filtered through celite
  2. customto remove catalyst
  3. concentrationconcentrated in vacuo
  4. custompurified by reverse phase HPLC on Phenominex column (250×20 mm)
  5. customover 30 min

Sources & evidence

ORD record
ord-5d2a18c8e26e426fbd87e175c915ae65
Source dataset
uspto-grants-2007_07
Patent number
US07244713B2

Reaction notes

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