HCID 86607293, compound → ((2R,3S,4R,5R)-5-(6-(((S)-2,3-dihydro-1H-inden-1-yl)amino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl sulfamate

HRID 552690Notes

Reaction equation

HRID 552690 reaction equation
[S:1](=[O:35])(=[O:34])([O:3][CH2:4][C@@H:5]1[C@@H:12]2[C@@H:8]([O:9]C(C)(C)[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[NH:24][C@@H:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27][CH2:26]2)[O:6]1)[NH2:2]>FC(F)(F)C(O)=O.O>[S:1](=[O:35])(=[O:34])([O:3][CH2:4][C@@H:5]1[C@@H:12]([OH:11])[C@@H:8]([OH:9])[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[NH:24][C@@H:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:27][CH2:26]2)[O:6]1)[NH2:2]

Participants

4

Reactant 1

HCID 86607293HCID 86607293, compound

Product 1

HCID 11655576((2R,3S,4R,5R)-5-(6-(((S)-2,3-dihydro-1H-inden-1-yl)amino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl sulfamateYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

((3aR,4R,6R,6aR)-6-{6-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]-9H-purin-9-yl}-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methyl sulfamate (400 mg, 0.80 mmol) was dissolved in a preformed mixture of trifluoroacetic acid (1.8 mL) and water (0.2 mL). The solution was allowed to stand at room temperature for 10 minutes and evaporated to dryness. This was twice evaporated from methanol and the residue was purified by reverse phase HPLC to yield 248 mg (67%) of final compound.

Workup

  1. customevaporated to dryness
  2. customThis was twice evaporated from methanol
  3. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-2289f815329548d08eec529730bc6734
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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