2-Fluorothiophenol → HCID 10434433, compound

HRID 916546

Reaction equation

HRID 916546 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[OH:9][C@@H:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[NH:15][C:16]1[N:24]=[CH:23][N:22]=[C:21]2[C:17]=1[N:18]=[CH:19][N:20]2[CH:25]1[C@H:29]([OH:30])[C@H:28]([OH:31])[C@@H:27]([CH2:32]Cl)[O:26]1>[OH-].[Na+].CN(C)C=O>[OH:9][C@@H:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[NH:15][C:16]1[N:24]=[CH:23][N:22]=[C:21]2[C:17]=1[N:18]=[CH:19][N:20]2[CH:25]1[C@H:29]([OH:30])[C@H:28]([OH:31])[C@@H:27]([CH2:32][S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[O:26]1

Participants

5

Reactant 2

HCID 5202162-FluorothiophenolHCID 671894862-{6-[((1R,2R)-2-hydroxycyclopentyl)amino]-purin-9-yl}(4S,5S,3R)-5-(chloromethyl)oxolane-3,4-diol

Product 1

HCID 10434433HCID 10434433, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 2-fluorothiophenol (38 mL, 406 mmol) in 2N sodium hydroxide (100 mL) was added 2-{6-[((1R,2R)-2-hydroxycyclopentyl)amino]purin-9-yl}(4S,5S,3R)-5-(chloromethyl)oxolane-3,4-diol (15.0 g, 40.6 mmol) in N,N-dimethylformamide (120 mL). The mixture was warmed to 100 C for 4 hours, following the progress of the reaction by TLC. The N,N-dimethylformamide was removed under reduced pressure, and the remaining mixture was diluted with water (200 mL), neutralized with acetic acid, extracted with ethyl acetate (3×125 mL), and the combined organic layers were dried over MgSO4. After removing the solvent under reduced pressure the residue was triturated with diethyl ether and filtered, to afford 16 grams of 2-{6-[((1R,2R)-2-hydroxycyclopentyl)amino]purin-9-yl}(4S,5 S,3R)-5-[(2-fluorophenylthio)methyl]oxolane-3,4-diol as a white powder (85% yield).

Workup

  1. temperatureThe mixture was warmed to 100 C for 4 hours
  2. customthe progress of the reaction by TLC
  3. customThe N,N-dimethylformamide was removed under reduced pressure
  4. additionthe remaining mixture was diluted with water (200 mL)
  5. extractionextracted with ethyl acetate (3×125 mL)
  6. dry with materialthe combined organic layers were dried over MgSO4
  7. customAfter removing the solvent under reduced pressure the residue
  8. customwas triturated with diethyl ether
  9. filtrationfiltered

Sources & evidence

ORD record
ord-7708bfa48b7543cd8670163582b4e2f7
Source dataset
uspto-grants-2007_09
Patent number
US07271157B2

Linked notes

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