Benzoyl chloride → 6-benzamido-9-((2R,3R,4S) 3,4-bis(hydroxymethyl)-oxetan-2-yl)purine

HRID 37392Notes

Reaction equation

HRID 37392 reaction equation
[OH:1][CH2:2][C@@H:3]1[C@@H:6]([CH2:7][OH:8])[O:5][C@H:4]1[N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[NH2:18].[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>N1C=CC=CC=1>[C:19]([NH:18][C:14]1[N:13]=[CH:12][N:11]=[C:10]2[C:15]=1[N:16]=[CH:17][N:9]2[C@H:4]1[C@H:3]([CH2:2][OH:1])[C@@H:6]([CH2:7][OH:8])[O:5]1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 72214Oxetanocin

Product 1

HCID 138899386-benzamido-9-((2R,3R,4S) 3,4-bis(hydroxymethyl)-oxetan-2-yl)purine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Under a nitrogen atmosphere, in a round-bottom flask were placed 2.5 g of 9-((2R,3R,4S)-3,4-bis-hyroxymethyl-oxetan-2-yl)adenine and 40 mL of pyridine. To the system, at 0° C., was added 4.6 g of benzoyl chloride, the cold bath was removed, and the reaction mixture was stirred at room temperature for 1 day. The reaction mixture was diluted with a small amount of acetone and poured into ice/water. The resulting precipitate was collected by suction filtration and treated with 20 mL of 1M aqueous sodium hydroxide in 40 mL of DMF. The reaction mixture was diluted with saturated aqueous sodium bicarbonate and extracted with several portions of chloroform. The chloroform extracts were dried (Na2SO4) and concentrated with a rotary evaporator, and the crude product was rinsed with ether and recrystallized from ethanol-water to obtain 6-benzamido-9-((2R,3R,4S) 3,4-bis(hydroxymethyl)-oxetan-2-yl)purine.

Workup

  1. customUnder a nitrogen atmosphere, in a round-bottom flask were placed
  2. customthe cold bath was removed
  3. additionThe reaction mixture was diluted with a small amount of acetone
  4. additionpoured into ice/water
  5. filtrationThe resulting precipitate was collected by suction filtration
  6. additiontreated with 20 mL of 1M aqueous sodium hydroxide in 40 mL of DMF
  7. additionThe reaction mixture was diluted with saturated aqueous sodium bicarbonate
  8. extractionextracted with several portions of chloroform
  9. dry with materialThe chloroform extracts were dried (Na2SO4)
  10. concentrationconcentrated with a rotary evaporator
  11. washthe crude product was rinsed with ether
  12. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-66de30aa894849e588ddf46103456ffd
Source dataset
uspto-grants-1995_05
Patent number
US05420276

Reaction notes

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