HCID 10696565, compound → Lodenosine

HRID 2301684Notes

Reaction equation

HRID 2301684 reaction equation
[F:1][C@H:2]1[CH2:6][C@@H:5]([CH2:7][O:8]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:4][C@H:3]1[N:28]1[CH:36]=[N:35][C:34]2[C:29]1=[N:30][CH:31]=[N:32][C:33]=2[NH2:37]>C(O)(=O)C>[F:1][C@H:2]1[CH2:6][C@@H:5]([CH2:7][OH:8])[O:4][C@H:3]1[N:28]1[CH:36]=[N:35][C:34]2[C:29]1=[N:30][CH:31]=[N:32][C:33]=2[NH2:37]

Participants

3

Reactant 1

HCID 10696565HCID 10696565, compound

Product 1

HCID 72180LodenosineYield 61.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

35.3 mg (0.0710 mmols) of 9-[2,3-dideoxy-2-fluoro-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl]-9H-purine-6-amine was dissolved in 1.0 ml of acetic acid, and stirred at room temperature for about 4 hours and then at 80° C. for about 3 hours. To this was added 1.0 ml of acetic acid, and cooled to room temperature. This was concentrated, and the residue formed was taken out and purified through a silica gel plate (using 91% methylene chloride/ethanol). The fraction of the intended product was extracted with methanol, and the solvent was evaporated out to obtain 11.1 mg (yield 61.5%) of the product which was white solid. The physical data of the product obtained herein were the same as those disclosed in the literature.

Workup

  1. waitat 80° C. for about 3 hours
  2. temperaturecooled to room temperature
  3. concentrationThis was concentrated
  4. customthe residue formed
  5. custompurified through a silica gel plate (using 91% methylene chloride/ethanol)
  6. extractionThe fraction of the intended product was extracted with methanol
  7. customthe solvent was evaporated out

Sources & evidence

ORD record
ord-cbd7364cac6a458bbc7f8f81928c223a
Source dataset
uspto-grants-2002_12
Patent number
US06500946B1

Reaction notes

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