Methanol → HCID 70348858, compound

HRID 2082275Notes

Reaction equation

HRID 2082275 reaction equation
[C@@H:1]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH3:29][OH:30]>N1C=CC=CC=1>[C:20]([N:15]([C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:14]1[C:13]2[N:12]=[CH:11][N:10]([C:19]=2[N:18]=[CH:17][N:16]=1)[C@@H:1]1[O:9][C@H:6]([CH2:7][O:8][C:29](=[O:30])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@:4]([C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([OH:5])[C@@:2]1([C:20](=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[OH:3])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 7412Benzoyl chlorideHCID 60961Adenosine

Product 1

HCID 70348858HCID 70348858, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of 5.34 g (20 mmole) adenosine (Sigma, dried at 80° C./10-3Torr for 24 h) in 100 ml dry pyridine, 33.74 g (240 mmole) benzoyl chloride was added dropwise. After 20 h stirring at room temperature ("r.t.") the mixture was treated with 16 ml dry MeOH and then extracted with CHCl3 (3×250 ml). The organic phase was washed with water (3×250 ml), dried over Na2SO4, and evaporated to dryness. Final coevaporation was performed with toluene. The residue was dissolved in CHCl3 /MeOH 2/1 by heating, and after cooling to r.t., petrolether (diethylether) was added until the solution became turbid. After standing for 12 h at 0° C. 12.18 g was obtained, and from the mother liquor, 2.66 g of the product were isolated as colorless needles of m.p. 183°-184° C., yield 14.84 g (94%).

Workup

  1. additionwas added dropwise
  2. extractionextracted with CHCl3 (3×250 ml)
  3. washThe organic phase was washed with water (3×250 ml)
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in CHCl3 /MeOH 2/1
  7. temperatureby heating
  8. temperatureafter cooling to r.t.
  9. additionpetrolether (diethylether) was added until the solution
  10. waitAfter standing for 12 h at 0° C
  11. custom12.18 g was obtained

Sources & evidence

ORD record
ord-70af6bdea9be44eabd536d8c20dae77c
Source dataset
uspto-grants-1993_02
Patent number
US05188897

Reaction notes

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