Acetonitrile → HCID 86654223, compound

HRID 552718Notes

Reaction equation

HRID 552718 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][C:7]2[N:15]=[CH:14][N:13]=[C:12]3[C:8]=2[N:9]=[CH:10][N:11]3[C@H:16]2[C@@H:20]3[O:21][C:22]([CH3:25])([CH3:24])[O:23][C@@H:19]3[C@@H:18]([CH2:26][OH:27])[O:17]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[S:38]([NH2:41])(=[O:40])=[O:39].C(#N)C>CN(C)C=O>[S:38](=[O:40])(=[O:39])([O:27][CH2:26][C@@H:18]1[C@@H:19]2[C@@H:20]([O:21][C:22]([CH3:25])([CH3:24])[O:23]2)[C@H:16]([N:11]2[CH:10]=[N:9][C:8]3[C:12]2=[N:13][CH:14]=[N:15][C:7]=3[CH2:6][C:5]2[CH:28]=[CH:29][C:2]([F:1])=[CH:3][CH:4]=2)[O:17]1)[NH2:41]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 67164416HCID 67164416, compound

Product 1

HCID 86654223HCID 86654223, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

{(3aR,4R,6R,6aR)-6-[6-(4-Fluorobenzyl)-9H-purin-9-yl]-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl}methanol (249 mg, 0.000622 mol) and triethylamine (173.4 μL, 0.001244 mol) were dissolved in dry N,N-dimethylformamide (10 mL) under nitrogen and the solution was cooled in a water/ice bath. A 2M solution of chlorosulfonamide in acetonitrile (0.0012 mol, 600 μL) was added dropwise. After 1.5 h, the reaction was quenched with methanol, concentrated in vacuo and the residue was purified by flash chromatography (DCM/EtOAc 30% to 80%) to obtain the product as an oil (262 mg, 88%).

Workup

  1. temperaturethe solution was cooled in a water/ice bath
  2. customthe reaction was quenched with methanol
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by flash chromatography (DCM/EtOAc 30% to 80%)

Sources & evidence

ORD record
ord-1289b7cd331343cb859d93b433320a76
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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