Acetic Acid → HCID 86595708, compound

HRID 1178691Notes

Reaction equation

HRID 1178691 reaction equation
[P:1]([O:13][CH2:14][C@H:15]1[O:20][CH2:19][C@@H:18]([N:21]2[CH:28]=[CH:27][C:25](=[O:26])[NH:24][C:22]2=[O:23])[CH2:17][C@@H:16]1[OH:29])([O:4][P:5]([O:8][P:9]([OH:12])([OH:11])=[O:10])([OH:7])=[O:6])(=[O:3])[OH:2].C(O)(=O)C.[CH2:34]([NH2:37])[CH:35]=[CH2:36].C(O)(=O)C>C([O-])(=O)C.[Na+].O>[P:1]([O:13][CH2:14][C@H:15]1[O:20][CH2:19][C@@H:18]([N:21]2[CH:28]=[C:27]([CH2:36][CH:35]=[CH:34][NH2:37])[C:25](=[O:26])[NH:24][C:22]2=[O:23])[CH2:17][C@@H:16]1[OH:29])([O:4][P:5]([O:8][P:9]([OH:11])([OH:12])=[O:10])([OH:7])=[O:6])(=[O:2])[OH:3]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 122036582-Propen-1-amine, acetateHCID 86595705HCID 86595705, compound

Product 1

HCID 86595708HCID 86595708, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 517045Sodium AcetateSolvent

Conditions

Temperature
50 °C

Procedure

100 mg (0.19 mmol)of 1,5-Anhydro-2-(uracil-1yl)-2,3-dideoxy-D-arabino-hexitol 6 triphosphate and 106 mg (0.33 mmol) mercury II acetate were dissolved in 5 ml 0.1 M sodium acetate buffer pH5 The mixture was stirred for 4 h at 50° C. after cooling to room temperature the mixture was diluted with 40 ml water. A freshly prepared allylamine acetate solution. (0.77 ml (13 mmol) were neutralized with 4M acetic acid) and 150 mg (1.5 mmol) dipotassium tetrachloropalladinate were added and the mixture was stirred for 24 h at room temperature. The reaction mixture was filtered through a 0.45 μm membrane filter and the filtrate was applied on a DEAE-Sephadex column and it was eluated with a gradient from 0.1-1 M Trieethylammoniumbicarbonate pH8 monitoring at 260 nm. The major UV peak was collected (Ninhydrine reaction positive) and further purified by reversed phase chromatography with a gradient from buffer 100% A: 0.1M triethylammonium acetate pH 8.0 to 100% buffer B: 0.1 M triethylammonium acetate/Acetonitril 1:1 monitoring at 260 nm on a RP 18 Hypersil column) The fractions containing the aminoallyl triphosphate were collected and evaporated under vacuum. The presence of the aminogroup was verified by ninhydrine reaction Excess triethylammonium-acetate was removed by several coevaporations with water. Yield 80 mg

Workup

  1. temperatureafter cooling to room temperature the mixture
  2. stirringthe mixture was stirred for 24 h at room temperature
  3. filtrationThe reaction mixture was filtered through a 0.45 μm membrane
  4. filtrationfilter
  5. customThe major UV peak was collected
  6. custom(Ninhydrine reaction positive)
  7. customfurther purified by reversed phase chromatography with a gradient from buffer 100% A
  8. addition0.1M triethylammonium acetate pH 8.0 to 100% buffer B: 0.1 M triethylammonium acetate/Acetonitril 1:1 monitoring at 260 nm on a RP 18 Hypersil column) The fractions containing the aminoallyl triphosphate
  9. customwere collected
  10. customevaporated under vacuum
  11. customThe presence of the aminogroup was verified by ninhydrine reaction Excess triethylammonium-acetate
  12. customwas removed by several coevaporations with water

Sources & evidence

ORD record
ord-4e99d28717394be1b3cbfbdc8c3bde4b
Source dataset
uspto-grants-2007_10
Patent number
US07276592B2

Reaction notes

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