HCID 86754790, compound → HCID 70107872, compound

HRID 1602565Notes

Reaction equation

HRID 1602565 reaction equation
[C:1]([O:5][C:6]([CH:8]([CH:14]([OH:54])[C:15](=[O:53])[N:16]([C@H:26]([CH3:52])[C@@H:27]([C:43]1[CH:48]=[CH:47][C:46]2[O:49][CH2:50][O:51][C:45]=2[CH:44]=1)[CH2:28][C:29]1[O:30][C:31]([C:34](=[O:42])[NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:32][CH:33]=1)[CH2:17]/[CH:18]=[CH:19]/[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[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]([OH:54])[C:15](=[O:53])[N:16]([C@H:26]([CH3:52])[C@@H:27]([C:43]1[CH:48]=[CH:47][C:46]2[O:49][CH2:50][O:51][C:45]=2[CH:44]=1)[CH2:28][C:29]1[O:30][C:31]([C:34](=[O:42])[NH:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:32][CH:33]=1)[CH2:17]/[CH:18]=[CH:19]/[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH2:9][C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 86754790HCID 86754790, compound

Product 1

HCID 70107872HCID 70107872, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolvent

Procedure

384 mg of methyl (3RS,4RS)-3-(tert-butoxycarbonyl)-4-hydroxy-4-[N-[(1R,2R)-1-methyl-2-(3, 4-methylenedioxyphenyl)-3-{5-(phenylcarbamoyl)-2-furyl}propyl]-N-{(E)-3-phenyl-2-propenyl}carbamoyl]butanoate was dissolved in 15 ml of acetonitrile and stirred together with 219 mg of tetrapropylammonium perruthenate at room temperature for 1 hour. The solvent was distilled off under reduced pressure, and the residue was preliminarily purified by silica gel short column chromatography [chloroform→methanol] and the purified again by silica gel column chromatography [hexane/ethyl acetate=2/1→3/2] to give 285 mg (yield: 74%) of the title compound as a colorless oily substance.

Workup

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

Sources & evidence

ORD record
ord-969242a50b974592a542121e8953aab7
Source dataset
uspto-grants-1999_11
Patent number
US05981573

Reaction notes

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