HCID 67520692, compound → HCID 59180376, compound

HRID 1925696Notes

Reaction equation

HRID 1925696 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([C:18]2[CH:22]=[CH:21][S:20][C:19]=2[C:23]([O:25][CH3:26])=[O:24])[CH2:15][O:16][CH3:17])(=[O:13])=[O:12])=[C:7]([CH:27]=[CH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]([C:18]2[CH:22]=[CH:21][S:20][C:19]=2[C:23]([O:25][CH3:26])=[O:24])[CH2:15][O:16][CH3:17])(=[O:12])=[O:13])=[C:7]([CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67520692HCID 67520692, compound

Product 1

HCID 59180376HCID 59180376, compoundYield 60.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 25 (206.0 mg; 0.47 mmol) and palladium on carbon (103.0 mg; 0.91 mmol) in ethanol (2.3 mL) was evacuated and filled with hydrogen gas (3×) and then stirred at room temperature under hydrogen overnight. Additional palladium on carbon (103.0 mg) was added and stirring was continued at room temperature for 16 hours. The reaction mixture filtered through celite and the filtrate concentrated under reduced pressure to afford the title compound as a clear oil (143 mg).

Workup

  1. customwas evacuated
  2. additionfilled with hydrogen gas (3×)
  3. additionAdditional palladium on carbon (103.0 mg) was added
  4. stirringstirring
  5. waitwas continued at room temperature for 16 hours
  6. filtrationThe reaction mixture filtered through celite
  7. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-c506f15ef3394fccb46e0b432222302f
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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