HCID 117653647, compound → HCID 89663443, compound

HRID 1486516Notes

Reaction equation

HRID 1486516 reaction equation
C([O:8][NH:9][C:10](=[O:40])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH2:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[CH3:34])=[C:26]([CH3:38])[CH:25]=2)([CH2:22][CH3:23])[CH2:20][CH3:21])=[CH:15][C:14]=1[CH3:39])C1C=CC=CC=1>CCOC(C)=O.[Pd]>[CH3:36][C:33]([CH3:34])([CH3:35])[C:32](=[O:37])[CH2:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([C:19]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:10]([NH:9][OH:8])=[O:40])=[C:14]([CH3:39])[CH:15]=2)([CH2:20][CH3:21])[CH2:22][CH3:23])=[CH:25][C:26]=1[CH3:38]

Participants

4

Reactant 1

HCID 117653647HCID 117653647, compound

Product 1

HCID 89663443HCID 89663443, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Compound 7 (21.9 mg, 0.0401 mmol) was dissolved in EtOAc (1.0 mL) and 10% Pd/C (4.3 mg, 0.43 mg Pd, 0.0040 mmol, 10 mol % Pd) was added and the reaction vessel purged (×4) with H2 (g). The reaction was stirred under a balloon of H2 (g) for 0.5 h, before being purged (×2) with Ar(g). The reaction mixture was filtered through a pad of celite and rinsed with EtOAc. The filtrate was concentrated in vacuo to give the crude hydroxamic acid which was purified by octadecyl functionalized silica gel column chromatography (0:100→100:0 MeOH/H2O) to afford the title hydroxamic acid (JF-B59) (14.6 mg, 80%). A portion of this (8.2 mg) was further purified, for biological testing, by HPLC (gradient elution, 50:50→95:5 MeOH/H2O over 20 mins at 3 mL/min on a semi-preparative Zorbax Rx-C18 column) to afford analytically pure compound (JF-B59) (6.9 mg, 68% extrapolated yield)

Workup

  1. customthe reaction vessel purged (×4) with H2 (g)
  2. custombefore being purged (×2) with Ar(g)
  3. filtrationThe reaction mixture was filtered through a pad of celite
  4. washrinsed with EtOAc
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto give the crude hydroxamic acid which
  7. customwas purified by octadecyl functionalized silica gel column chromatography (0:100→100:0 MeOH/H2O)

Sources & evidence

ORD record
ord-b4b9a72416ff4a7a82d1e633b5928e2c
Source dataset
uspto-grants-2016_08
Patent number
US09428447B2

Reaction notes

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