Furfuryl Alcohol → (s)-3-((s)-2-Benzyloxycarbonylamino-4-methyl-valerylamino)-1-furfuryloxy-4-phenyl-2-butanone

HRID 356142

Reaction equation

HRID 356142 reaction equation
[N+](=[CH:3]C(C=[N+]=[N-])=O)=[N-].[CH2:9]([O:16][C:17]([NH:19][C@H:20]([C:25]([NH:27][C@H:28]([C:36](O)=[O:37])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:26])[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:39]([OH:45])[C:40]1[O:44][CH:43]=[CH:42][CH:41]=1>C(Cl)Cl.C([O-])(=O)C.[Rh+3].C([O-])(=O)C.C([O-])(=O)C>[CH2:9]([O:16][C:17]([NH:19][C@@H:20]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:25]([NH:27][C@@H:28]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:36](=[O:37])[CH2:3][O:45][CH2:39][C:40]1[O:44][CH:43]=[CH:42][CH:41]=1)=[O:26])=[O:18])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 7361Furfuryl AlcoholHCID 131720047N-Benzyloxycarbonyl-L-leucyl-L-phenylalanine diazomethylketone

Product 1

HCID 53799632(s)-3-((s)-2-Benzyloxycarbonylamino-4-methyl-valerylamino)-1-furfuryloxy-4-phenyl-2-butanoneYield 7.4%

Reagents, catalysts & solvents 2

HCID 168478Rhodium acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

N-Benzyloxycarbonyl-L-leucyl-L-phenylalanine diazomethylketone (314 mg) was dissolved in furfuryl alcohol (2 ml) and methylene chloride (1 ml). To the solution was added rhodium acetate (II) dimer (10 mg). After the mixture was stirred at room temperature for 1 hour, the solvents was removed in vacuo and the residue was chromatographed on a silica gel column, eluting with hexane-ethyl acetate to give the titled product (27 mg).

Workup

  1. customthe solvents was removed in vacuo
  2. customthe residue was chromatographed on a silica gel column
  3. washeluting with hexane-ethyl acetate

Sources & evidence

ORD record
ord-24754fe988254e4286cea2e607a0575e
Source dataset
uspto-grants-1998_11
Patent number
US05834508

Linked notes

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