HCID 22026369, compound → HCID 70663095, compound

HRID 2272943Notes

Reaction equation

HRID 2272943 reaction equation
[CH2:1]([O:8][C:9]([CH:11]1[C:17](=[C:18]2[CH2:22][CH:21]([CH2:23]I)[O:20][C:19]2=[O:25])[O:16][C@H:15]2[N:12]1[C:13](=[O:26])[CH2:14]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.COC(C)(C)C>C(OCC)(=O)C.[Pd]>[CH2:1]([O:8][C:9]([CH:11]1[C:17](=[C:18]2[CH2:22][CH:21]([CH3:23])[O:20][C:19]2=[O:25])[O:16][C@H:15]2[N:12]1[C:13](=[O:26])[CH2:14]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 22026369HCID 22026369, compoundHCID 70663156HCID 70663156, compound

Product 1

HCID 70663095HCID 70663095, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 1800 mg of 10% Pd/C and 390 ml of ethyl acetate is stirred at room temperature under hydrogen atmosphere for 30 minutes. A solution of the compound of Example 41 (800 mg) in 10 ml of ethyl acetate is introduced with a syringe, and stirring is continued under hydrogen atmosphere. At time points of 1 hour 20 minutes, 2 hour 40 minutes, 4 hour and 5 hour 35 minutes further amounts of 1800 mg 10% Pd/C each are added. After a total reaction time of 6 hours 50 minutes, the mixture is filtered through celite and stripped of the solvents to obtain a residue which is subjected to chromatography thrice over SiO2 using toluene/t-butyl methyl ether (17/1). The title compound is obtained as a foam, having characterization data as indicated below.

Workup

  1. stirringstirring
  2. filtrationAfter a total reaction time of 6 hours 50 minutes, the mixture is filtered through celite
  3. customto obtain a residue which

Sources & evidence

ORD record
ord-25c8c96ef44c4efa9d809263f1315078
Source dataset
uspto-grants-2015_09
Patent number
US09120808B2

Reaction notes

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