Sodium Iodide → [(3aR,4R,6R,6aR)-6-(6-iodo-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl sulfamate

HRID 552745Notes

Reaction equation

HRID 552745 reaction equation
[S:1](=[O:26])(=[O:25])([O:3][CH2:4][C@@H:5]1[C@@H:12]2[C@@H:8]([O:9][C:10]([CH3:14])([CH3:13])[O:11]2)[C@H:7]([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][CH:18]=[N:19][C:20]=3Cl)[O:6]1)[NH2:2].[Na+].[I-:28].FC(F)(F)C(O)=O>CC(=O)CC>[S:1](=[O:26])(=[O:25])([O:3][CH2:4][C@@H:5]1[C@@H:12]2[C@@H:8]([O:9][C:10]([CH3:14])([CH3:13])[O:11]2)[C@H:7]([N:15]2[CH:23]=[N:22][C:21]3[C:16]2=[N:17][CH:18]=[N:19][C:20]=3[I:28])[O:6]1)[NH2:2]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 6422Trifluoroacetic acidHCID 86607326((3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate

Product 1

HCID 86607325[(3aR,4R,6R,6aR)-6-(6-iodo-9H-purin-9-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methyl sulfamateYield 81.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
-10 °C

Procedure

To a solution of ((3aR,4R,6R,6aR)-6-(6-chloro-9H-purin-9-yl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate (645 mg, 1.59 mmol) in 2-butanone (30.0 mL) was added NaI (4.77 g, 31.79 mmol). The reaction was cooled to −10° C. and trifluoroacetic acid (612 μL, 7.94 mmol) was added. The reaction was stirred for 4.5 hours, quenched with saturated aq NaHCO3 and extracted with DCM. The crude product was purified by flash chromatography (40% EtOAc/DCM) to isolate the title compound (0.642 g, 81%).

Workup

  1. customquenched with saturated aq NaHCO3
  2. extractionextracted with DCM
  3. customThe crude product was purified by flash chromatography (40% EtOAc/DCM)

Sources & evidence

ORD record
ord-2e50882845e64956ab458ec7cd7a55ad
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

Loading…