HCID 86607328, compound → HCID 58296231, compound

HRID 552750Notes

Reaction equation

HRID 552750 reaction equation
[S:1](=[O:37])(=[O:36])([O:3][CH2:4][C@@H:5]1[C@@H:9]([O:10][Si](C(C)(C)C)(C)C)[CH2:8][C@H:7]([N:18]2[C:22]3[N:23]=[CH:24][N:25]=[C:26]([NH:27][C:28](=[O:35])[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:21]=3[CH:20]=[CH:19]2)[O:6]1)[NH2:2]>N1C=CC=CC=1.C1COCC1.N1C=CC=CC=1>[S:1](=[O:36])(=[O:37])([O:3][CH2:4][C@@H:5]1[C@@H:9]([OH:10])[CH2:8][C@H:7]([N:18]2[C:22]3[N:23]=[CH:24][N:25]=[C:26]([NH:27][C:28](=[O:35])[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:21]=3[CH:20]=[CH:19]2)[O:6]1)[NH2:2]

Participants

4

Reactant 1

HCID 86607328HCID 86607328, compound

Product 1

HCID 58296231HCID 58296231, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 16069498Pyridine tetrahydrofuranSolvent

Procedure

To a solution of ((2R,3S,5R)-5-[4-(benzoylamino)-7H-pyrrolo[2,3-d]pyrimidin-7-yl]-3-{[tert-butyl(dimethyl)silyl]oxy}tetrahydrofuran-2-yl)methyl sulfamate (0.292 g, 0.533 mmol) in 5.4 mL pyridine/THF (1:1) was added approximately 5 drops of hydrofluoridic acid in pyridine. The solution was stirred at r.t. overnight, quenched by slowly adding saturated aq NaHCO3 (20 mL) and extracted with DCM (2×25 mL) and EtOAc (25 mL). The organics were combined, dried (Na2SO4), filtered, and concentrated. The crude material was purified by flash chromatography (1 to 10% MeOH/DCM) to afford the final compound (0.177 g, 77%).

Workup

  1. customquenched by slowly adding saturated aq NaHCO3 (20 mL)
  2. extractionextracted with DCM (2×25 mL) and EtOAc (25 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography (1 to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-dfe425238dad4fa5a35202e16192d3ac
Source dataset
uspto-grants-2011_05
Patent number
US07951810B2

Reaction notes

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