HCID 86755320, compound → HCID 70296054, compound

HRID 1004327Notes

Reaction equation

HRID 1004327 reaction equation
[C:1]([O:5][C:6]([CH:8]([CH:14]([C:16](=[O:52])[N:17]([CH:27]([CH3:51])[CH:28]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:29][C:30]1[O:31][C:32]([C:35](=[O:43])[NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[CH:33][CH:34]=1)[CH2:18]/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[OH:15])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(#N)C.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]([O:5][C:6]([C:8](=[C:14]([C:16](=[O:52])[N:17]([CH:27]([CH3:51])[CH:28]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:29][C:30]1[O:31][C:32]([C:35](=[O:43])[NH:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[CH:33][CH:34]=1)[CH2:18]/[CH:19]=[CH:20]/[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[OH:15])[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86755320HCID 86755320, compound

Product 1

HCID 70296054HCID 70296054, compoundYield 76.3%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

92 mg of methyl (3RS,4RS)-3-(tert-butoxycarbonyl)-4-[N-[(1RS,2RS)-2-(tert-butoxycarbonyl)-1-methyl-3-{5-(phenylcarbamoyl)-2-furyl}propyl]-N-{(E)-3-phenyl-2-propenyl}carbamoyl]-4-hydroxybutanoate was dissolved in 3 ml of acetonitrile and stirred with 56 mg of tetrapropylammonium perruthenate at room temperature for 2 hours. The solvent was distilled off under reduced pressure, and the residue was roughly purified by silica gel short column chromatography [chloroform→methanol] and purified again by silica gel column chromatography [hexane/ethyl acetate=2/1→3/2] to give 70 mg (yield: 76%) of the title compound as a colorless oily substance.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was roughly purified by silica gel short column chromatography [chloroform→methanol]
  3. custompurified again by silica gel column chromatography [hexane/ethyl acetate=2/1→3/2]

Sources & evidence

ORD record
ord-81b38ceccf504bb489da2e839b83c9fb
Source dataset
uspto-grants-2000_04
Patent number
US06048894

Reaction notes

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