HCID 68044582, compound → HCID 68044639, compound

HRID 1524378Notes

Reaction equation

HRID 1524378 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:20]([NH:22][CH2:23][CH2:24][CH:25]([F:49])[CH2:26][C@@H:27]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[N:28]([S:32]([C:35]1[CH:40]=[CH:39][C:38]([N+:41]([O-])=O)=[CH:37][CH:36]=1)(=[O:34])=[O:33])[CH:29]([CH3:31])[CH3:30])=[O:21])[CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4]>[Pd].C(OCC)(=O)C>[CH3:1][O:2][C:3]([NH:5][C@H:6]([C:20]([NH:22][CH2:23][CH2:24][CH:25]([F:49])[CH2:26][C@@H:27]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[N:28]([S:32]([C:35]1[CH:40]=[CH:39][C:38]([NH2:41])=[CH:37][CH:36]=1)(=[O:34])=[O:33])[CH:29]([CH3:31])[CH3:30])=[O:21])[CH:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:4]

Participants

4

Reactant 1

HCID 68044582HCID 68044582, compound

Product 1

HCID 68044639HCID 68044639, compoundYield 77.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To the material from Step 6 (31 mg, 0.044 mmol) and 10% palladium on carbon (5 mg, 0.004 mmol) was added ethyl acetate (0.5 mL). The reaction mixture was purged with nitrogen, and stirred under hydrogen (1 atm) overnight. Upon addition of DCM, the reaction mixture was filtered through celite, washed with dichloromethane, and the filtrate was concentrated in vacuo. The residue was purified by column chromatography on silica gel using ethyl acetate-hexanes (0:100 to 90:10) to afford 23 mg of the title compound as a colorless foam. LCMS (M+1)=671.

Workup

  1. customThe reaction mixture was purged with nitrogen
  2. additionUpon addition of DCM
  3. filtrationthe reaction mixture was filtered through celite
  4. washwashed with dichloromethane
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-dd8361cd261b4516895cff39368ad4db
Source dataset
uspto-grants-2015_07
Patent number
US09079834B2

Reaction notes

Loading…