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

HRID 356142
Notes
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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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 acetateCatalyst
HCID 6344
Dichloromethane
Solvent

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
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05834508

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes