Carbon Dioxide → HCID 178444210, compound

HRID 275561Notes

Reaction equation

HRID 275561 reaction equation
[PH:1](=[O:4])([OH:3])[OH:2].[CH2:5]([C:7]([CH2:38][CH3:39])([CH:9]([S:34]C(=O)C)[C:10]1[N:14]=[CH:13][N:12]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]=1)[CH3:8])[CH3:6].C[O-].[Na+].C(=O)=O.O>CO>[PH:1](=[O:2])([OH:4])[OH:3].[CH2:38]([C:7]([CH2:5][CH3:6])([CH:9]([SH:34])[C:10]1[N:14]=[CH:13][N:12]([C:15]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:11]=1)[CH3:8])[CH3:39]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 962WaterHCID 10942334Sodium MethoxideHCID 178444218HCID 178444218, compound

Product 1

HCID 178444210HCID 178444210, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of diethyl 3-acetylthio-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (0.71 g, prepared as described in Example 37) in methanol (20 ml) was added dropwise, under nitrogen, to a stirred solution of sodium methoxide (from 0.06 g sodium) in methanol (10 ml), whilst maintaining the temperature below 5° C. The mixture was allowed to attain room temperature and to stand for twenty hours, neutralized with solid carbon dioxide, poured into water and extracted with ethyl acetate. The extracts were washed with water and brine, dried over magnesium sulphate and evaporated under reduced pressure. The residue was chromatographed on silica, using dichloromethane-ethanol (49:1) as eluant, to give diethyl 3-mercapto-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (0.35 g) as a colourless gum. NMR (CDCl3): δ1.3(6H,dt), 1.7-2.0(2H,m), 2.2-2.4(2H,m), 4.0(4H,m), 4.1(1H,m), 7.1(6H,m), 7.3(9H,m), 7.9(1H,s). M/S: M+ 521.

Workup

  1. temperaturewhilst maintaining the temperature below 5° C
  2. customto attain room temperature
  3. waitto stand for twenty hours
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with water and brine
  6. dry with materialdried over magnesium sulphate
  7. customevaporated under reduced pressure
  8. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-6c9f6f52dbf64342b9fc0ad7d9c0c49a
Source dataset
uspto-grants-1995_02
Patent number
US05393732

Reaction notes

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