p-Toluenesulfonic acid monohydrate → 1-(2,2-difluoro-2-deoxy-beta-D-ribofuranosyl)-4-(2-propyl-1-oxopentyl)aminopyrimidin-2-one Mono-p-toluenesulfonate

HRID 1640394Notes

Reaction equation

HRID 1640394 reaction equation
[F:1][C:2]1([F:27])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:25])[CH:18]([CH2:22][CH2:23][CH3:24])[CH2:19][CH2:20][CH3:21])=[N:12][C:11]1=[O:26].O.[C:29]1([CH3:39])[CH:34]=[CH:33][C:32]([S:35]([OH:38])(=[O:37])=[O:36])=[CH:31][CH:30]=1>C(OC(C)C)(=O)C>[C:29]1([CH3:39])[CH:30]=[CH:31][C:32]([S:35]([OH:38])(=[O:36])=[O:37])=[CH:33][CH:34]=1.[F:27][C:2]1([F:1])[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:25])[CH:18]([CH2:19][CH2:20][CH3:21])[CH2:22][CH2:23][CH3:24])=[N:12][C:11]1=[O:26]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 11646777Ly-2334737

Product 1

HCID 237251391-(2,2-difluoro-2-deoxy-beta-D-ribofuranosyl)-4-(2-propyl-1-oxopentyl)aminopyrimidin-2-one Mono-p-toluenesulfonateYield 68%

Reagents, catalysts & solvents 1

HCID 7915Isopropyl AcetateSolvent

Procedure

Dissolve 1-(2,2-difluoro-2-deoxy-β-D-ribofuranosyl)-4-(2-propyl-1-oxopentyl)aminopyrimidin-2-one (400 mg, 1.03 mmol) at room temperature in isopropyl acetate (5 mL). Add para-toluenesulfonic acid monohydrate (195 mg, 1.03 mmol) to the solution. After complete dissolution, immediate precipitation of a white solid occurs. Stir the slurry for 10 minutes. Filter the solid product by vacuum filtration, wash with methanol (1 mL), and air dry to give the title compound (392 mg, 68%).

Workup

  1. dissolutionAfter complete dissolution, immediate precipitation of a white solid
  2. filtrationFilter the solid product
  3. filtrationby vacuum filtration
  4. washwash with methanol (1 mL), and air
  5. customdry

Sources & evidence

ORD record
ord-5e76fd7fa01145f1ab70c37e8aa47a76
Source dataset
uspto-grants-2012_02
Patent number
US08114854B2

Reaction notes

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