Hydrochloric Acid → HCID 86742607, compound

HRID 414162Notes

Reaction equation

HRID 414162 reaction equation
[P:1]([O:5][CH2:6][C@H:7]1[O:11][C@@H:10]([N:12]2[C:24]3[N:23]=[CH:22][N:21]=[C:16]([NH:17][CH2:18][CH2:19][NH2:20])[C:15]=3[N:14]=[CH:13]2)[C@H:9]([OH:25])[C@@H:8]1[OH:26])([OH:4])([OH:3])=[O:2].C(=O)(O)[O-].[Na+].F[C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:34]=1[N+:42]([O-:44])=[O:43].Cl.[OH-].[Na+]>O.C(O)C>[P:1]([O:5][CH2:6][C@H:7]1[O:11][C@@H:10]([N:12]2[C:24]3[N:23]=[CH:22][N:21]=[C:16]([NH:17][CH2:18][CH2:19][NH:20][C:37]4[CH:38]=[CH:33][C:34]([N+:42]([O-:44])=[O:43])=[CH:35][C:36]=4[N+:39]([O-:41])=[O:40])[C:15]=3[N:14]=[CH:13]2)[C@H:9]([OH:25])[C@@H:8]1[OH:26])([OH:4])([OH:3])=[O:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6264Dinitrofluorobenzene2×HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 114747595'-Adenylic acid, N-(2-aminoethyl)-

Product 1

HCID 86742607HCID 86742607, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

Two hundred fifty mg N6 -(2-aminoethyl)adenosine-5'-monophosphate (0.65 mmol) from Part A of this Example was dissolved in 20 ml water at pH 8. Then 168 mg sodium bicarbonate was added, followed by 0.2 ml 1-fluoro-2,4-dinitrobenzene (1.58 mmol dissolved in 2 ml ethanol). The reaction mixture was stirred in the dark at room temperature for 4 hr and then an additional 0.1 ml 1-fluoro-2,4-dinitrobenzene in 1 ml ethanol was added. After the reaction mixture had stirred overnight, it was adjusted to pH 2.0 with hydrochloric acid and was poured into 200 ml ethanol. The precipitate which formed was dissolved in 200 ml water and this solution was adjusted to pH 8.0 with sodium hydroxide and chromatographed on a 2.5×30 cm column of DEAE-cellulose in the bicarbonate form (available from Reeve Angel, Clifton, N.J.). The chromatogram was developed with a linear gradient generated with 1.5 liters water and 1.5 liters 0.7 M ammonium bicarbonate. A major peak of yellow material which absorbed uv light was eluted between 1200 and 1500 ml of the gradient. Ammonium bicarbonate was removed by repeated evaporation to dryness to give 40 percent yield of the desired product. This product migrated as one yellow spot on thin-layer chromatograms developed with the same two solvents mentioned in Part A of this Example and on epichlorohydrintriethanolamine anion-exchange paper developed with 0.25M sodium acetate-acetic acid buffer, pH 5.0. In 0.02N hydrochloric acid the product had optical absorption maxima of 264 nm and 363 nm with millimolar extinction coefficients of 21.8 and 14.2, respectively.

Workup

  1. stirringAfter the reaction mixture had stirred overnight
  2. customThe precipitate which formed
  3. customchromatographed on a 2.5×30 cm column of DEAE-cellulose in the bicarbonate form (available from Reeve Angel, Clifton, N.J.)
  4. customA major peak of yellow material which absorbed uv light
  5. washwas eluted between 1200 and 1500 ml of the gradient
  6. customAmmonium bicarbonate was removed
  7. customevaporation to dryness

Sources & evidence

ORD record
ord-630c59c286554e03b0f0577389424547
Source dataset
uspto-grants-1988_12
Patent number
US04791055

Reaction notes

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