HCID 178447792, compound → HCID 178447793, compound

HRID 582167Notes

Reaction equation

HRID 582167 reaction equation
[PH:1](=[O:4])([OH:3])[OH:2].[CH:5]([C:8]([CH:36]([CH3:38])[CH3:37])([F:35])/[CH:9]=[CH:10]/[C:11]1[N:15]=[CH:14][N:13]([C:16]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:12]=1)([CH3:7])[CH3:6]>C(O)(C)C.[Pd]>[PH:1](=[O:2])([OH:4])[OH:3].[CH:36]([C:8]([CH:5]([CH3:7])[CH3:6])([F:35])[CH2:9][CH2:10][C:11]1[N:15]=[CH:14][N:13]([C:16]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:12]=1)([CH3:37])[CH3:38]

Participants

4

Reactant 1

HCID 178447792HCID 178447792, compound

Product 1

HCID 178447793HCID 178447793, compoundYield 38.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolvent

Procedure

Diisopropyl E-1-fluoro-3(1-trityl-1,2,4-triazol-3-yl)prop-2-ene phosphonate (0.62 g, prepared as described in Example 19), was hydrogenated in dry isopropanol (10 ml) over 10% palladium on carbon (0.20 g) over a period of five days. The solution was filtered through Hyflo Super-Cel and evaporated under reduced pressure. The residue was chromatographed on silica, using ethyl acetate then ethyl acetate-ethanol (9:1) as eluant, to give diisopropyl 1-fluoro-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (0.24 g) as a colourless gum. NMR (CDCl3): δ 1.3(12H,m), 2.3(2H,m), 3.0(2H,m), 4.7(2H,m and 1H,m), 7.05-7.4(15H,m), 7.85(1H,s). The structure was confirmed by 13C and 31P NMR. M/S: MH+ 536. Other fractions gave detritylated material (0.18 g), also as a clear gum.

Workup

  1. filtrationThe solution was filtered through Hyflo Super-Cel
  2. customevaporated under reduced pressure
  3. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-d5063557ab594e6faa6d90ccfdcb3a65
Source dataset
uspto-grants-1999_07
Patent number
US05922644

Reaction notes

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